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HIDE GRAPHICAL ABSTRACTS
Viacheslav Petrov,
Rebecca J. Dooley,
Alexander A. Marchione,
Elizabeth L. Diaz,
Brittany S. Clem and
William Marshall
Beilstein J. Org. Chem. 2020, 16, 2739–2748, doi:10.3762/bjoc.16.224
were prepared by the reaction of 2,2,4,4 -tetrakis (trifluoromethyl )-1,3 -dithietane (1) with the corresponding substrates, resulting in the selective alkylation of one of the nitrogen atoms of the imidazole ring. The reaction proceeds under mild conditions in a polar solvent, giving the alkylated
formation of a new derivative of caffeine.
Keywords: adenine; caffeine; cyclic dimer of hexafluorothioacetone; hexafluoroisopropyl group; purine; 2,2,4,4 -tetrakis (trifluoromethyl )-1,3 -dithietane ; theophylline; Introduction
Despite significant progress in the last 20–30 years, the selective introduction of
, and the conversion of the ketoester into an amino acid [2]; and the reaction of aldehydes with either Ph3P/(CF3)2CCl2 [3] or 2,2,4,4 -tetrakis (trifluoromethyl )-1,3 -dithietane [4][5]. The last method was employed in the synthesis of 16,16,16,17,17,17-hexafluororetinal, as reported by the Haas group [5
Scheme 1:
Reaction of purine (2 ) with tetrakis(trifluoromethyl)-1,3-dithietane (1 ).
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Figure 1:
Crystal structure of 2a , with the thermal ellipsoids drawn at 30% probability.
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Scheme 2:
Reaction of 4-azabenzimidazole (3 ) with tetrakis(trifluoromethyl)-1,3-dithietane (1 ).
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Scheme 4:
Reaction of adenine (5 ) and 2-fluoroadenine (6 ) with tetrakis(trifluoromethyl)-1,3-dithietane (1 ).
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Scheme 5:
Reaction of theophylline (7 ) with tetrakis(trifluoromethyl)-1,3-dithietane (1 ).
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Figure 2:
Crystal structure of 7a , with the thermal ellipsoids drawn at 30% probability.
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Scheme 6:
Probable mechanism of the reaction of tetrakis(trifluoromethyl)-1,3-dithietane (1 ) with compounds 2 –...
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Figure 3:
Top: 19 F NMR spectra of 3a acquired over a sample temperature range of 223–373 K. Left: Fitted plot...
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Figure 4:
DFT-optimized structures of the two rotamers of 3a . Left: Lower-energy rotamer. Right: Higher-energ...
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Beilstein J. Org. Chem. 2020, 16, 1357–1410, doi:10.3762/bjoc.16.116
2,2,4,4 -tetrakis (trifluoromethyl )-1,3 -dithietane -generated bis(trifluoromethyl)thioacetone with various olefins in nucleophilic solvents DMF or DMSO. Previously, the reaction of 2,2,4,4 -tetrakis (trifluoromethyl )-1,3 -dithietane (363) and quadricyclane (218) was carried out in diglyme in the presence of CsF
-tetrakis (trifluoromethyl )-1,3 -dithietane (363) with electron-rich olefins 371 and 372a gave the corresponding thietanes 374 and 375a. On the other hand, reacting 2,2,4,4 -tetrakis (trifluoromethyl )-1,3 -dithietane (363) with 2,3-dihydrofuran (373) gave the corresponding fused thietane 6,6-bis(trifluoromethyl
(trifluoromethyl )-1,3 -dithietane (363) with alkyl vinyl ethers 371 or phenyl vinyl sulfide (372b) in DMSO at 70 °C afforded the corresponding 2,2-bis(trifluoromethyl)-3-alkoxy/phenylthiothietanes 374 and 375b, respectively, with 1,3-dithiolanes 382 as byproducts [101] (Scheme 78).
The reactions of 2,2,4,4 -tetrakis
Figure 1:
Examples of biologically active thietane-containing molecules.
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Scheme 1:
Synthesis of 1-(thietan-2-yl)ethan-1-ol (10 ) from 3,5-dichloropentan-2-ol (9 ).
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Scheme 2:
Synthesis of thietanose nucleosides 2 ,14 from 2,2-bis(bromomethyl)propane-1,3-diol (11 ).
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Scheme 3:
Synthesis of methyl 3-vinylthietane-3-carboxylate (19 ).
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Scheme 5:
Synthesis of 6-amino-2-thiaspiro[3.3]heptane hydrochloride (28 ).
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Scheme 6:
Synthesis of optically active thietane 31 from vitamin C.
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Scheme 7:
Synthesis of an optically active thietane nucleoside from diethyl L-tartrate (32 ).
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Scheme 8:
Synthesis of thietane-containing spironucleoside 40 from 5-aldo-3-O -benzyl-1,2-O -isopropylidene-α-D...
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Scheme 9:
Synthesis of optically active 2-methylthietane-containing spironucleoside 43 .
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Scheme 10:
Synthesis of a double-linked thietane-containing spironucleoside 48 .
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Scheme 11:
Synthesis of two diastereomeric thietanose nucleosides via 2,4-di(benzyloxymethyl)thietane (49 ).
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Scheme 12:
Synthesis of the thietane-containing PI3k inhibitor candidate 54 .
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Scheme 13:
Synthesis of the spirothietane 57 as the key intermediate to Nuphar sesquiterpene thioalkaloids.
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Scheme 14:
Synthesis of spirothietane 61 through a direct cyclic thioetherification of 3-mercaptopropan-1-ol.
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Scheme 16:
Synthesis of thietanylbenzimidazolone 75 from (iodomethyl)thiazolobenzimidazole 70 .
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Scheme 17:
Synthesis of 2-oxa-6-thiaspiro[3.3]heptane (80 ) from bis(chloromethyl)oxetane 76 and thiourea.
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Scheme 18:
Synthesis of the thietane-containing glycoside, 2-O -p -toluenesulfonyl-4,6-thioanhydro-α-D-gulopyran...
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Scheme 19:
Synthesis of methyl 4,6-thioanhydro-α-D-glucopyranoside (89 ).
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Scheme 23:
Synthesis of anhydro-thiohexofuranosides 110 , 112 and 113 from from 1,2:4,5-di-O -isopropylidene D-f...
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Scheme 24:
Synthesis of optically active thietanose nucleosides from D- and L-xyloses.
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Scheme 28:
Synthesis of thietane-3-ols 145 from (1-chloromethyl)oxiranes 142 and hydrogen sulfide.
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Scheme 29:
Synthesis of thietane-3-ol 145a from chloromethyloxirane (142a ).
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Scheme 30:
Synthesis of thietane-3-ols 145 from 2-(1-haloalkyl)oxiranes 142 and 147 with ammonium monothiocarb...
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Scheme 31:
Synthesis of 7-deoxy-5(20)thiapaclitaxel 154a , a thietane derivative of taxoids.
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Scheme 32:
Synthesis of 5(20)-thiadocetaxel 158 from 10-deacetylbaccatin III (155 ).
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Scheme 33:
Synthesis of thietane derivatives 162 as precursors for deoxythiataxoid synthesis through oxiraneme...
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Scheme 35:
Mechanism for the formation of the thietane ring in 171 from oxiranes with vicinal leaving groups 1 ...
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Scheme 36:
Synthesis of cis- 2,3-disubstituted thietane 175 from thiirane-2-methanol 172 .
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Scheme 37:
Synthesis of a bridged thietane 183 from aziridine cyclohexyl tosylate 179 and ammonium tetrathiomo...
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Scheme 38:
Synthesis of thietanes via the photochemical [2 + 2] cycloaddition of thiobenzophenone 184a with va...
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Scheme 39:
Synthesis of spirothietanes through the photo [2 + 2] cycloaddition of cyclic thiocarbonyls with ol...
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Scheme 40:
Photochemical synthesis of spirothietane-thioxanthenes 210 from thioxanthenethione (208 ) and butatr...
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Scheme 41:
Synthesis of thietanes 213 from 2,4,6-tri(tert -butyl)thiobenzaldehyde (211 ) with substituted allene...
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Scheme 42:
Photochemical synthesis of spirothietanes 216 and 217 from N -methylthiophthalimide (214 ) with olefi...
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Scheme 43:
Synthesis of fused thietanes from quadricyclane with thiocarbonyl derivatives 219 .
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Scheme 44:
Synthesis of tricyclic thietanes via the photo [2 + 2] cycloaddition of N -methyldithiosuccinimides ...
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Scheme 45:
Synthesis of tricyclic thietanes via the photo [2 + 2] cycloaddition of N -methylthiosuccinimide/thi...
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Scheme 46:
Synthesis of tricyclic thietanes via the photo [2 + 2] cycloaddition of N -alkylmonothiophthalimides...
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Scheme 47:
Synthesis of spirothietanes from dithiosuccinimides 223 with 2,3-dimethyl-2-butene (215a ).
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Scheme 48:
Synthesis of thietanes 248a ,b from diaryl thione 184b and ketene acetals 247a ,b .
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Scheme 49:
Photocycloadditions of acridine-9-thiones 249 and pyridine-4(1H )-thione (250 ) with 2-methylacrynitr...
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Scheme 50:
Synthesis of thietanes via the photo [2 + 2] cycloaddition of mono-, di-, and trithiobarbiturates 2 ...
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Scheme 51:
Synthesis of spirothietanes via the photo [2 + 2] cycloaddition of 1,1,3-trimethyl-2-thioxo-1,2-dih...
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Scheme 52:
Synthesis of spirothietanes via the photo [2 + 2] cycloaddition of thiocoumarin 286 with olefins.
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Scheme 53:
Photochemical synthesis of thietanes 296 –299 from semicyclic and acyclic thioimides 292 –295 and 2,3...
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Scheme 54:
Photochemical synthesis of spirothietane 301 from 1,3,3-trimethylindoline-2-thione (300 ) and isobut...
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Scheme 55:
Synthesis of spirobenzoxazolethietanes 303 via the photo [2 + 2] cycloaddition of alkyl and aryl 2-...
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Scheme 56:
Synthesis of spirothietanes from tetrahydrothioxoisoquinolines 306 and 307 with olefins.
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Scheme 57:
Synthesis of spirothietanes from 1,3-dihydroisobenzofuran-1-thiones 311 and benzothiophene-1-thione...
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Scheme 58:
Synthesis of 2-triphenylsilylthietanes from phenyl triphenylsilyl thioketone (316 ) with electron-po...
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Scheme 59:
Diastereoselective synthesis of spiropyrrolidinonethietanes 320 via the photo [2 + 2] cycloaddition...
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Scheme 60:
Synthesis of bicyclic thietane 323 via the photo [2 + 2] cycloaddition of 2,4-dioxo-3,4-dihydropyri...
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Scheme 61:
Photo-induced synthesis of fused thietane-2-thiones 325 and 326 from silacyclopentadiene 324 and ca...
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Scheme 62:
Synthesis of highly strained tricyclic thietanes 328 via the intramolecular photo [2 + 2] cycloaddi...
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Scheme 63:
Synthesis of tri- and pentacyclic thietanes 330 and 332 , respectively, through the intramolecular p...
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Scheme 64:
Synthesis of tricyclic thietanes 334 via the intramolecular photo [2 + 2] cycloaddition of N -vinylt...
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Scheme 65:
Synthesis of tricyclic thietanes 336 via the intramolecular photo [2 + 2] cycloaddition of N -but-3-...
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Scheme 66:
Synthesis of tricyclic thietanes via the intramolecular photo [2 + 2] cycloaddition of N -but-3-enyl...
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Scheme 67:
Synthesis of tetracyclic thietane 344 through the intramolecular photo [2 + 2] cycloaddition of N -[...
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Scheme 68:
Synthesis of tri- and tetracyclic thietanes 348 , 350 , and 351 , through the intramolecular photo [2 ...
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Scheme 69:
Synthesis of tetracyclic fused thietane 354 via the photo [2 + 2] cycloaddition of vinyl 2-thioxo-3H ...
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Scheme 70:
Synthesis of highly rigid thietane-fused β-lactams via the intramolecular photo [2 + 2] cycloadditi...
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Scheme 71:
Asymmetric synthesis of a highly rigid thietane-fused β-lactam 356a via the intramolecular photo [2...
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Scheme 72:
Diastereoselective synthesis of the thietane-fused β-lactams via the intramolecular photo [2 + 2] c...
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Scheme 73:
Asymmetric synthesis of thietane-fused β-lactams 356 via the intramolecular photo [2 + 2] cycloaddi...
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Scheme 74:
Synthesis of the bridged bis(trifluoromethyl)thietane from 2,2,4,4-tetrakis(trifluoromethyl)-1,3-di...
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Scheme 75:
Synthesis of the bridged-difluorothietane 368 from 2,2,4,4-tetrafluoro-1,3-dithietane (367 ) and qua...
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Scheme 76:
Synthesis of bis(trifluoromethyl)thietanes from 2,2,4,4-tetrakis(trifluoromethyl)-1,3-dithietane (3 ...
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Scheme 77:
Synthesis of 2,2-dimethylthio-4,4-di(trifluoromethyl)thietane (378 ) from 2,2,4,4-tetrakis(trifluoro...
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Scheme 78:
Formation of bis(trifluoromethyl)thioacetone (381 ) through nucleophilic attack of dithietane 363 by...
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Scheme 79:
Synthesis of 2,2-bis(trifluoromethyl)thietanes from 2,2,4,4-tetrakis(trifluoromethyl)-1,3-dithietan...
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Scheme 80:
Synthesis of the bridged bis(trifluoromethyl)thietane 364 from of 2,2,4,4-tetrakis(trifluoromethyl)...
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Scheme 81:
Synthesis of 2,4-diiminothietanes 390 from alkenimines and 4-methylbenzenesulfonyl isothiocyanate (...
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Scheme 82:
Synthesis of arylidene 2,4-diiminothietanes 393 starting from phosphonium ylides 391 and isothiocya...
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Scheme 83:
Synthesis of thietane-2-ylideneacetates 397 through a DABCO-catalyzed formal [2 + 2] cycloaddition ...
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Scheme 84:
Synthesis of 3-substituted thietanes 400 from (1-chloroalkyl)thiiranes 398 .
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Scheme 85:
Synthesis of N -(thietane-3-yl)azaheterocycles 403 and 404 through reaction of chloromethylthiirane (...
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Scheme 86:
Synthesis of 3-sulfonamidothietanes 406 from sulfonamides and chloromethylthiirane (398a ).
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Scheme 87:
Synthesis of N -(thietane-3-yl)isatins 408 from chloromethylthiirane (398a ) and isatins 407 .
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Scheme 88:
Synthesis of 3-(nitrophenyloxy)thietanes 410 from nitrophenols 409 and chloromethylthiirane (398a ).
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Scheme 89:
Synthesis of N -aryl-N -(thietane-3-yl)cyanamides 412 from N -arylcyanamides 411 and chloromethylthiir...
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Scheme 90:
Synthesis of 1-(thietane-3-yl)pyrimidin-2,4(1H ,3H )-diones 414 from chloromethylthiirane (398a ) and ...
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Scheme 91:
Synthesis of 2,4-diiminothietanes 418 from 2-iminothiiranes 416 and isocyanoalkanes 415 .
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Scheme 92:
Synthesis of 2-vinylthietanes 421 from thiiranes 419 and 3-chloroallyl lithium (420 ).
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Scheme 93:
Synthesis of thietanes from thiiranes 419 and trimethyloxosulfonium iodide 424 .
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Scheme 94:
Mechanism for synthesis of thietanes 425 from thiiranes 419 and trimethyloxosulfonium iodide 424 .
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Scheme 95:
Synthesis of functionalized thietanes from thiiranes and dimethylsulfonium acylmethylides.
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Scheme 96:
Mechanism for the rhodium-catalyzed synthesis of functionalized thietanes 429 from thiiranes 419 an...
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Scheme 97:
Synthesis of 3-iminothietanes 440 through thermal isomerization from 4,5-dihydro-1,3-oxazole-4-spir...
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Scheme 98:
Synthesis of thietanes 443 from 3-chloro-2-methylthiolane (441 ) through ring contraction.
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Scheme 99:
Synthesis of an optically active thietanose 447 from D-xylose involving a ring contraction.
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Scheme 100:
Synthesis of optically thietane 447 via the DAST-mediated ring contraction of 448 .
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Scheme 101:
Synthesis of the optically thietane nucleoside 451 via the ring contraction of thiopentose in 450 .
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Scheme 102:
Synthesis of spirothietane 456 from 3,3,5,5-tetramethylthiolane-2,4-dithione (452 ) and benzyne (453 ...
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Scheme 103:
Synthesis of thietanes 461 via photoisomerization of 2H ,6H -thiin-3-ones 459 .
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Scheme 104:
Phosphorodithioate-mediated synthesis of 1,4-diarylthietanes 465 .
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Scheme 105:
Mechanism of the phosphorodithioate-mediated synthesis of 1,4-diarylthietanes 465 .
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Scheme 106:
Phosphorodithioate-mediated synthesis of trisubstituted thietanes (±)-470 .
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Scheme 107:
Mechanism on the phosphorodithioate-mediated synthesis of trisubstituted thietanes.
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Scheme 108:
Phosphorodithioate-mediated synthesis of thietanes (±)-475 .
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Scheme 109:
Phosphorodithioate-mediated synthesis of 1,2-disubstituted thietanes from aldehydes 476 and acrylon...
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Scheme 110:
Phosphorodithioate-mediated synthesis of 1,2-disubstituted thietanes via a one-pot three-component ...
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Scheme 111:
Mechanism for the phosphorodithioate-mediated synthesis of 1,2-disubstituted thietanes via three-co...
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Scheme 112:
Phosphorodithioate-mediated synthesis of substituted 3-nitrothietanes.
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Scheme 113:
Mechanism on the phosphorodithioate-mediated synthesis of 1,2-disubstituted thietanes (±)-486 .
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Scheme 115:
Asymmetric synthesis of optically active 2,4-diarylthietanes.
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Scheme 116:
Synthesis of 3-acetamidothietan-2-one 503 via the intramolecular thioesterification of 3-mercaptoal...
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Scheme 117:
Synthesis of 4-substituted thietan-2-one via the intramolecular thioesterification of 3-mercaptoalk...
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Scheme 118:
Synthesis of 4,4-disubstituted thietan-2-one 511 via the intramolecular thioesterification of the 3...
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Scheme 119:
Synthesis of a spirothietan-2-one 514 via the intramolecular thioesterification of 3-mercaptoalkano...
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Scheme 120:
Synthesis of thiatetrahydrolipstatin starting from (S )-(−)-epichlorohydrin ((S )-142a ).
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Scheme 121:
Synthesis of 2-phenethyl-4-(propan-2-ylidene)thietane (520 ) from 5-bromo-6-methyl-1-phenylhept-5-en...
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Scheme 122:
Synthesis of 2-phenethyl-4-(propan-2-ylidene)thietane (520 ) directly from S -(5-bromo-6-methyl-1-phe...
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Scheme 123:
Synthesis of 2-alkylidenethietanes from S -(2-bromoalk-1-en-4-yl)thioacetates.
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Scheme 124:
Synthesis of 2-alkylidenethietanes from S -(2-bromo/chloroalk-1-en-4-yl)thiols.
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Scheme 125:
Synthesis of spirothietan-3-ol 548 from enone 545 and ammonium hydrosulfide.
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Scheme 126:
Asymmetric synthesis of the optically active thietanoside from cis -but-2-ene-1,4-diol (47 ).
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Scheme 127:
Synthesis of 2-alkylidenethietan-3-ols 557 via the fluoride-mediated cyclization of thioacylsilanes ...
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Scheme 128:
Synthesis of 2-iminothietanes via the reaction of propargylbenzene (558 ) and isothiocyanates 560 in...
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Scheme 129:
Synthesis of 2-benzylidenethietane 567 via the nickel complex-catalyzed electroreductive cyclizatio...
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Scheme 130:
Synthesis of 2-iminothietanes 569 via the photo-assisted electrocyclic reaction of N -monosubstitute...
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Scheme 131:
Synthesis of ethyl 3,4-diiminothietane-2-carboxylates from ethyl thioglycolate (570 ) and bis(imidoy...
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Scheme 132:
Synthesis of N -(thietan-3-yl)-α-oxoazaheterocycles from azaheterocyclethiones and chloromethyloxira...
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Scheme 133:
Synthesis of thietan-3-yl benzoate (590 ) via the nickel-catalyzed intramolecular reductive thiolati...
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Scheme 134:
Synthesis of 2,2-bis(trifluoromethyl)thietane from 3,3-bis(trifluoromethyl)-1,2-dithiolane.
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Scheme 135:
Synthesis of thietanes from enamines and sulfonyl chlorides.
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Scheme 136:
Synthesis of spirothietane 603 via the [2 + 3] cycloaddition of 2,2,4,4-tetramethylcyclobutane-1,3-...
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Scheme 137:
Synthesis of thietane (605 ) from 1-bromo-3-chloropropane and sulfur.
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