Aspergiloid I, an unprecedented spirolactone norditerpenoid from the plant-derived endophytic fungus Aspergillus sp. YXf3

• Zhi Kai Guo,
• Rong Wang,
• Wei Huang,
• Xiao Nian Li,
• Rong Jiang,
• Ren Xiang Tan and
• Hui Ming Ge

Beilstein J. Org. Chem. 2014, 10, 2677–2682, doi:10.3762/bjoc.10.282

• Autopol III polarimeter. The UV spectrum was obtained on a Hitachi U-3000 spectrophotometer. The CD spectrum was measured on a JASCO J-810 spectrometer, and the IR spectrum (KBr) was obtained on a Nexus 870 FTIR spectrometer. NMR data were acquired using a Bruker AVANCE III-500 NMR spectrometer at 500 MHz

• (−0.53), 500 (+1.19) nm; IR (KBr) νmax 3649, 1735, 1700, 1652, 1558, 1540, 1508, 1457, 816 cm−1; 1H and 13C NMR data, see Table 1; HRMS–ESI (m/z): [M + Na]+ calcd for C18H26O4Na, 329.1723; found, 329.1729. X-ray crystallographic analysis of 1 Colorless crystal of 1 was obtained by crystallizing from a

One-pot four-component reaction for convenient synthesis of functionalized 1-benzamidospiro[indoline-3,4'-pyridines]

• Chao Wang,
• Yan-Hong Jiang and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2014, 10, 2671–2676, doi:10.3762/bjoc.10.281

• apparatus: All reactions were monitored by TLC. Melting points were taken on a hot-plate microscope apparatus. IR spectra were obtained on a Bruker Tensor 27 spectrometer (KBr disc). 1H and 13C NMR spectra were recorded with a Bruker AV-600 spectrometer with DMSO-d6 as solvent and TMS as internal standard

• , DMSO-d6) δ 177.3, 166.8, 163.6, 161.9, 152.1, 145.2, 141.3, 136.2, 135.2, 132.6, 131.1, 129.5, 128.6, 128.5, 128.4, 127.9, 127.6, 127.3, 124.1, 123.5, 122.8, 118.5, 108.8, 58.4, 52.9, 51.9, 49.4, 43.5; IR (KBr) υ: 3456, 2952, 2186, 1708, 1654, 1613, 1575, 1482, 1432, 1302, 1224, 1183, 1133, 1091, 1029

Design and synthesis of novel bis-annulated caged polycycles via ring-closing metathesis: pushpakenediol

• Sambasivarao Kotha and
• Mirtunjay Kumar Dipak

Beilstein J. Org. Chem. 2014, 10, 2664–2670, doi:10.3762/bjoc.10.280

• evaporated under reduced pressure and the residue was purified by silica gel column chromatography (5% ethyl acetate/petroleum ether) to give 20 (80 mg, 80%) as a thick pale yellow liquid. IR (KBr) νmax: 3073, 2974, 1752, 1636, 924 cm−1; 1H NMR (400 MHz, CDCl3) δ 1.82 (d, J = 11.4 Hz, 1H), 2.12 (d, J = 11.4

• . After the removal of the solvent under reduced pressure, the residue was purified by silica gel column chromatography (4% ethyl acetate/petroleum ether) to give 21 (280 mg, 70%) as a white solid. Mp: 158–160 °C; IR (KBr) νmax: 3309, 3055, 2977, 1265, 743, 705 cm−1; 1H NMR (400 MHz, CDCl3) δ 1.3 (1/2 ABq

• evaporated and the resulting residue was purified by silica gel column chromatography (25% ethyl acetate/petroleum ether) to give 22 (15 mg, 72%) as a white crystalline solid. Mp: 206–207 °C; IR (KBr) νmax: 3691, 3054, 2987, 2305, 1422, 1266 cm−1; 1H NMR (400 MHz, CDCl3) δ 1.38 (1/2 AB q, J1 = J2 = 11.0 Hz

Preparation of neuroprotective condensed 1,4-benzoxazepines by regio- and diastereoselective domino Knoevenagel–[1,5]-hydride shift cyclization reaction

• László Tóth,
• Yan Fu,
• Hai Yan Zhang,
• Attila Mándi,
• Katalin E. Kövér,
• Tünde-Zita Illyés,
• Attila Kiss-Szikszai,
• Balázs Balogh,
• Tibor Kurtán,
• Sándor Antus and
• Péter Mátyus

Beilstein J. Org. Chem. 2014, 10, 2594–2602, doi:10.3762/bjoc.10.272

• (100 MHz, CDCl3) δ 46.3 (C-3), 85.8 (C-2), 122.4 (C-9), 123.7 (C-7), 125.9 (C-5a), 126.3 (C-2’, C-6’), 128.5 (C-4’), 128.7 (C-3’, C-5’), 130.9 (C-6), 133.3 (C-8), 139.0 (C-1’), 154.5 (C-9a), 170.9 (C-5); IR (KBr) ν: 1462, 1665, 2917, 3075, 3203, 3307 cm−1; HRMS–ESI (m/z): [M + Na]+ calcd for

• ), 128.4 (C-3’, C-5’), 129.0 (C-4’, C-6), 135.6 (C-5a), 140.5 (C-1’), 159.1 (C-9a); IR (KBr) ν: 1579, 2935, 3328 cm−1; HRMS–ESI (m/z): [M + H]+ calcd for C15H16NO, 226.1232; found, 226.1235; Anal. calcd for C15H15NO (225.11): C, 79.97; H, 6.71; N, 6.22; found: C, 80.03; H, 6.76; N, 6.18. 5-Nitro-2-(2

• ’), 156.8 (C-9a), 158.2 (C-1”), 188.3 (CHO); IR (KBr) ν: 1382, 1500, 1681, 1734, 2921 cm−1; HRMS–ESI (m/z): [M + Na]+ calcd for C22H18N2O4Na, 397.1164; found, 397.1158; Anal. calcd for C22H18N2O4 (374.12): C, 70.58; H, 4.85; N, 7.48; found: C, 70.59; H, 4.89; N, 7.45. trans-1,3-Dimethyl-11'-nitro-2'-phenyl

Synthesis and characterization of a hyper-branched water-soluble β-cyclodextrin polymer

• Francesco Trotta,
• Fabrizio Caldera,
• Roberta Cavalli,
• Andrea Mele,
• Carlo Punta,
• Lucio Melone,
• Franca Castiglione,
• Barbara Rossi,
• Monica Ferro,
• Vincenza Crupi,
• Domenico Majolino,
• Valentina Venuti and
• Dominique Scalarone

Beilstein J. Org. Chem. 2014, 10, 2586–2593, doi:10.3762/bjoc.10.271

• , operating with a Globar source, in combination with a KBr beamsplitter, a DTGS/KBr detector. The powders were contained in Golden Gate diamond ATR system, just based on the ATR technique. The spectra were recorded in dry atmosphere, to avoid dirty contributions, with a resolution of 2 cm−1, automatically

Loose-fit polypseudorotaxanes constructed from γ-CDs and PHEMA-PPG-PEG-PPG-PHEMA

• Tao Kong,
• Lin Ye,
• Ai-ying Zhang and
• Zeng-guo Feng

Beilstein J. Org. Chem. 2014, 10, 2461–2469, doi:10.3762/bjoc.10.257

• a Shimadzu IR Prestige-21 FTIR spectrometer at room temperature in the range between 4000 and 500 cm−1, with a resolution of 2 cm−1 and 25 averaged scans. Samples were prepared by mixing with dry KBr powder. Differential scanning calorimetry (DSC) measurements were run on a SHIMADZU DSC-60

New highlights of the syntheses of pyrrolo[1,2-a]quinoxalin-4-ones

• Emilian Georgescu,
• Alina Nicolescu,
• Florentina Georgescu,
• Florina Teodorescu,
• Daniela Marinescu,
• Ana-Maria Macsim and
• Calin Deleanu

Beilstein J. Org. Chem. 2014, 10, 2377–2387, doi:10.3762/bjoc.10.248

• are uncorrected. The IR spectra were recorded on a Nicolet Impact 410 spectrometer, in KBr pellets. The high performance liquid chromatography (HPLC) analyses were performed with an Agilent Chromatograph 1200 Series at room temperature by isocratic elution of acrylonitrile on an Agilent Zorbax SB-C18

Molecular recognition of AT-DNA sequences by the induced CD pattern of dibenzotetraaza[14]annulene (DBTAA)–adenine derivatives

• Marijana Radić Stojković,
• Marko Škugor,
• Łukasz Dudek,
• Jarosław Grolik,
• Julita Eilmes and
• Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2175–2185, doi:10.3762/bjoc.10.225

• potassium carbonate (0.026 g, 0.189 mmol) were then added, and the stirring was continued for 24 h at room temperature. The reaction mixture was partitioned between dichloromethane (20 mL) and water (100 mL). A small amount of solid KBr was added to improve the separation of the phases. The organic layer

The effect of permodified cyclodextrins encapsulation on the photophysical properties of a polyfluorene with randomly distributed electron-donor and rotaxane electron-acceptor units

• Aurica Farcas,
• Ana-Maria Resmerita,
• Pierre-Henri Aubert,
• Flavian Farcas,
• Iuliana Stoica and
• Anton Airinei

Beilstein J. Org. Chem. 2014, 10, 2145–2156, doi:10.3762/bjoc.10.222

• . Acetonitrile (ACN) (Fischer), DCM, CHCl3, toluene and all other solvents were purchased from commercial sources (Sigma-Aldrich, Fisher) and used without further purification. 1H NMR spectra were recorded in toluene on a Bruker Advance 400 MHz instrument. The FTIR (KBr pellets) spectra were obtained on a Bruker

• 16 hours, dissolved in toluene and precipitated with methanol, filtered, washed with acetone, and dried. 0.301 g (35.5% yields) of a yellow solid was obtained after drying. FTIR (KBr, cm−1): 3439, 2958, 2853, 2370 (CN), 2344, 1721, 1632, 1412, 1367, 1319, 1251, 1147, 1096, 1045, 966, 885, 841, 750

• similar experimental conditions as described above except that TMS-γ-CD was used instead of TMS-β-CD. The copolymer was obtained as a yellow solid in 31.3% yield. FTIR (KBr, cm−1) 3439, 2957, 2925, 2854, 2371 (CN), 2343, 1743, 1611, 1541, 1510, 1462, 1440, 1413, 1366, 1298, 1251, 1152, 1097, 1045, 966; 1H

Isoxazolium N-ylides and 1-oxa-5-azahexa-1,3,5-trienes on the way from isoxazoles to 2H-1,3-oxazines

• Alexander F. Khlebnikov,
• Mikhail S. Novikov,
• Yelizaveta G. Gorbunova,
• Ekaterina E. Galenko,
• Kirill I. Mikhailov,
• Viktoriia V. Pakalnis and
• Margarita S. Avdontceva

Beilstein J. Org. Chem. 2014, 10, 1896–1905, doi:10.3762/bjoc.10.197

• Bruker FTIR spectrometer Tensor 27 by using KBr disks and only characteristic absorption bands are indicated. Single crystal X-ray data were collected by means of an Agilent Technologies Supernova Atlas and an Agilent Technologies Excalibur Eos diffractometer. The crystals were kept at 100 K during data

• (KBr, cm−1) ν: 1743 (C=O); crystal data for 3a: C20H19NO3, M = 321.36, monoclinic, space group P21/n, a = 10.2806(4), b = 10.5164(3), c = 15.3771(4) Å, β = 98.241(3)°, V = 1645.32(9) Å3, Z = 4, F(000) = 680, Dcalc = 1.297 mg m−3, μ = 0.704 mm−1. 8556 reflections were collected yielding 3164 unique

• , CDCl3) δ 14.2, 17.0, 23.3, 62.0, 85.1, 116.0, 127.6, 128.6, 130.4, 135.1, 159.2, 166.2, 168.4; ESIMS (m/z): calcd for C14H18NO3+, 260.1281; found, 260.1281; IR (KBr, cm−1) ν: 1737 (C=O). Methyl 2,4,6-triphenyl-2H-1,3-oxazine-2-carboxylate (3d) Compound 3d (245 mg, 66%; 70% based on consumed isoxazole

A promising cellulose-based polyzwitterion with pH-sensitive charges

• Thomas Elschner and
• Thomas Heinze

Beilstein J. Org. Chem. 2014, 10, 1549–1556, doi:10.3762/bjoc.10.159

• Europe and were used without further treatment. Cellulose phenyl carbonate was prepared by esterification of cellulose, dissolved in N,N-dimethylacetamide (DMAc)/LiCl, applying pyridine and phenyl chloroformate [21]. 1, DS 1.92 (determined by means of 1H NMR spectroscopy after peracetylation), FTIR (KBr

• Nicolet AVATAR 370 DTGS spectrometer (Thermo Scientific, Schwerte, Germany) with the KBr technique. Elemental analyses were performed by a CHNS 932 Analyzer (Leco, Mönchengladbach, Germany). Nephelometric measurements were carried out with a Turbiquant® 3000 IR from Merck (Darmstadt, Germany). The self

• and dried in vacuum at 40 °C. Yield: 90%, DSβ-alanine ester 0.88, DSBoc-EDA 0.95 (determined by elemental analysis from nitrogen content assuming a total DS of 1.83 according to a conversion of carbonate of 95% [21]), FTIR (KBr): 1716 cm−1 (νC=O, carbamate and ester); 13C NMR (100 MHz, MeOD) δ 172.0

Bis(β-lactosyl)-[60]fullerene as novel class of glycolipids useful for the detection and the decontamination of biological toxins of the Ricinus communis family

• Hirofumi Dohi,
• Takeru Kanazawa,
• Akihiro Saito,
• Keita Sato,
• Hirotaka Uzawa,
• Yasuo Seto and
• Yoshihiro Nishida

Beilstein J. Org. Chem. 2014, 10, 1504–1512, doi:10.3762/bjoc.10.155

• -500 spectrometer. HRMS–ESI spectra were recorded with a Thermo Scientific Exactive mass spectrometer. FTIR spectra were recorded on a JASCO FTIR-230 spectrometer (Japan) as KBr films. Ricin (2.5 mg mL−1) was obtained from Honen Corporation (now J-Oil Mills, Inc., Tokyo, Japan) in a 10 mmol L−1

Pyrene-modified PNAs: Stacking interactions and selective excimer emission in PNA₂DNA triplexes

• Alex Manicardi,
• Lucia Guidi,
• Alice Ghidini and
• Roberto Corradini

Beilstein J. Org. Chem. 2014, 10, 1495–1503, doi:10.3762/bjoc.10.154

• Nicolet 5700, in transmission mode using KBr or NaCl. HPLC–UV–MS were recorded by using a Waters Alliance 2695 HPLC with Micromass Quattro microAPI spectrometer, a Waters 996 PDA and equipped with a Phenomenex Jupiter column (250 × 4.6 mm, 5 μm, C18, 300 Å) (method A, 5 minutes in H2O 0.2% formic acid (FA

Hindered aryl bromides for regioselective palladium-catalysed direct arylation at less favourable C5-carbon of 3-substituted thiophenes

• Rongwei Jin,
• Charles Beromeo Bheeter and
• Henri Doucet

Beilstein J. Org. Chem. 2014, 10, 1239–1245, doi:10.3762/bjoc.10.123

• , allow the preparation of 2,5-diarylthiophenes with two different aryl units in two steps. The major byproduct of these couplings is KBr/AcOH instead of metallic salts as with more classical coupling procedures. For these reasons, this process gives an economically viable access to C5-arylated 3

Solid-phase-supported synthesis of morpholinoglycine oligonucleotide mimics

• Tatyana V. Abramova,
• Sergey S. Belov,
• Yulia V. Tarasenko and
• Vladimir N. Silnikov

Beilstein J. Org. Chem. 2014, 10, 1151–1158, doi:10.3762/bjoc.10.115

• negative mode in The Center of Cooperative Use (“Proteomics”, Russian Academy of Sciences). IR spectra were recorded on a Vector 22 spectrometer (Bruker Optics, Germany) in KBr. Quantitative analytical RPC were performed on a Milichrom A02 chromatograph system (Econova, Russia) on a ProntoSIL 125 C18

Regioselective S_N2' Mitsunobu reaction of Morita–Baylis–Hillman alcohols: A facile and stereoselective synthesis of α-alkylidene-β-hydrazino acid derivatives

• Silong Xu,
• Jian Shang,
• Junjie Zhang and
• Yuhai Tang

Beilstein J. Org. Chem. 2014, 10, 990–995, doi:10.3762/bjoc.10.98

• (TMS) as the internal standard. High resolution ESI mass spectra were acquired with an IonSpec QFT-ESI instrument. IR spectra were recorded on a Nicolet Avatar 330 FTIR spectrometer (in KBr). Column chromatography was performed on silica gel (200–300 mesh) using a mixture of petroleum ether (bp 60–90

Nonanebis(peroxoic acid): a stable peracid for oxidative bromination of aminoanthracene-9,10-dione

• Vilas Venunath Patil and
• Ganapati Subray Shankarling

Beilstein J. Org. Chem. 2014, 10, 921–928, doi:10.3762/bjoc.10.90

• protocol has a broad scope for the bromination of various substituted and unsubstituted aminoanthracene-9,10-diones. Keywords: aminoanthracene-9,10-dione; benzanthrone; KBr; nonanebis(peroxoic acid); oxidative bromination; Introduction The brominated aminoanthracene-9,10-dione derivatives and

• substrate and KBr as a source of bromine. Various solvents were screened (Table 2 entry 1–10) among which, acetic acid was found to be more effective than other solvents. It neutralizes the KOH formed during the reaction. To validate the usability of other aliphatic acids, we carried out the reaction in

• . It was surmised that, the oxidant nonanebis(peroxoic acid) oxidizes the KBr to Br+ (Scheme 2). During this process, KOH is formed, which is neutralized by the acetic acid. The bromonium ion thus formed reacts with the amine to give the brominated product. In case of unsubstituted amines, ortho

Cuevaenes C–E: Three new triene carboxylic derivatives from Streptomyces sp. LZ35ΔgdmAI

• Jing-Jing Deng,
• Chun-Hua Lu,
• Yao-Yao Li,
• Shan-Ren Li and
• Yue-Mao Shen

Beilstein J. Org. Chem. 2014, 10, 858–862, doi:10.3762/bjoc.10.82

• ) as an internal standard. HRMS–ESI were carried out on an LTQ-Orbitrap XL. Optical rotations were measured on a GYROMAT-HP polarimeter. The IR spectra (KBr) were obtained on a Nicolet iN10 Micro FTIR Microscope (Thermo Scientific). Reversed-phase (RP) C18 silica gel for column chromatography was

• 274 nm) to yield 2 (tR 7.6 min, 2 mg). Cuevaene C (3): light yellow powder; [a]D20 +230.0 (c 0.175, MeOH); HRMS–ESI m/z: [M + H]+ calcd for C21H22O5, 355.1540; found, 355.1544; IR (KBr) vmax: 3278, 1686, 1619, 1596, and 1463 cm−1. See Table 1 for the NMR data. Cuevaene D (4): light yellow powder; [a

• ]D20 +130.0 (c 0.315, MeOH); HRMS–ESI m/z: [M + H]+, (calcd for C21H23NO4, 354.4190; found, 354.4193; IR (KBr) vmax: 3347, 3220, 1660, 1615, 1591, and 1461 cm−1. For the NMR data see Table 1. Cuevaene E (5): white oil; [a]D20 +25.0 (c 0.08, MeOH); HRMS–ESI m/z: [M + H]+, (calcd for C21H23NO4, 354.4190

Columnar/herringbone dual crystal packing of pyrenylsumanene and its photophysical properties

• Binod Babu Shrestha,
• Shuhei Higashibayashi and
• Hidehiro Sakurai

Beilstein J. Org. Chem. 2014, 10, 841–847, doi:10.3762/bjoc.10.80

• through Celite, and evaporated. The residue was purified by GPC to afford pure 1 (10.0 mg, 84%). Characterization data Pyrenylsumanene (1) Mp: 255 °C; IR (KBr) ν: 3039, 2895, 2780, 1396, 842, 788, 725, 683, 602, 488, 418 cm−1; 1H NMR (CDCl3) δ 8.68 (s, 1H), 8.20–7.99 (m, 7H), 7.71 (s, 1H), 7.40 (s, 1H

Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems

• Alexander F. Khlebnikov,
• Mikhail S. Novikov,
• Viktoriia V. Pakalnis,
• Roman O. Iakovenko and
• Dmitry S. Yufit

Beilstein J. Org. Chem. 2014, 10, 784–793, doi:10.3762/bjoc.10.74

• spectrometers. IR spectra were recorded on a Bruker TENSOR 27 spectrometer for tablets in KBr. Single-crystal X-ray data for 3a were collected at 100 K on a Bruker Proteum R diffractometer (FR-591 rotating anode generator, Pt-135 CCD detector) equipped with Cobra (Oxford Cryosystems) open-flow cryostat. Data

• , 131.1, 134.5, 137.4, 160.2, 164.9; IR (KBr, cm−1) ν: 1721 (C=O); HRMS–ESI: [M + Na]+ calcd for C26H19NNaO4+, 432.1206; found, 432.1192; Anal. calcd for C26H19NO4: C, 76.27; H, 4.68; N, 3.42; found: C, 76.57; H, 4.47; N, 3.66; Crystal data for 3a: C26H19NO4, M = 409.42, monoclinic, space group P 21/n, a

• , 2H), 5.90 (s, 2H), 7.36–7.44 (m, 12H), 7.51–7.54 (m, 4H), 7.70–7.74 (m, 4H); 13C NMR (CDCl3) δ 47.9, 91.7, 98.7, 126.0, 126.3, 128.4, 128.7, 129.6, 131.3, 131.5, 138.4, 161.5, 163.2; IR (KBr, cm−1) ν 1674 (C=O); HRMS–ESI: [M + H]+ calcd for C34H27N2O4+, 527.1965; found, 527.1937. (6aRS,12aSR)-2,6a

Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira–Glaser cyclization sequence

• Fabian Klukas,
• Alexander Grunwald,
• Franziska Menschel and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2014, 10, 672–679, doi:10.3762/bjoc.10.60

• ((C7H5O)+, 22), 89 (14), 77 ((C6H5)+, 51), 63 (13), 51 (22); IR (KBr): = 1479 (w) cm−1, 1446 (w), 1155 (w), 1022 (m), 925 (w), 910 (w), 794 (m), 756 (s), 689 (s), 671 (m). Anal. calcd for C16H12O (220.3): C 87.25, H 5.49; Found: C 87.09, H 5.42; UV–vis (CH2Cl2): λmax(ε): 327 nm (35000 L·mol−1·cm−1), 342

One-pot three-component synthesis and photophysical characteristics of novel triene merocyanines

• Christian Muschelknautz,
• Robin Visse,
• Jan Nordmann and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2014, 10, 599–612, doi:10.3762/bjoc.10.51

• (CH), 127.5 (CH), 128.2 (CH), 128.3 (CH), 128.4 (CH), 128.6 (CH), 129.0 (CH), 129.5 (CH), 132.5 (CH), 154.4 (Cquat), 167.5 (Cquat); EIMS (70 eV) m/z (% relative intensity): 544 ([37Cl–M]+, 23), 542 ([35Cl–M]+, 100), 382 ([C25H1835ClNO]+, 22), 158 ([C11H12N]+, 38); IR (KBr) : 3080, 3053, 2968, 2924

• ), 321 (11), 306 (11), 291 (12), 222 (11), 218 (37), 144 (33), 142 (47), 132 (27), 127 (22), 117 (16), 105 (53), 91 (100); IR (KBr) : 3051, 2964, 2924, 2862, 1691, 1577, 1504, 1485, 1465, 1454, 1442, 1400, 1367, 1334, 1315, 1290, 1246, 1217, 1176, 1161, 1130, 1161, 1130, 1116, 1085, 1076, 1060, 1018

Tuning the interactions between electron spins in fullerene-based triad systems

• Maria A. Lebedeva,
• Thomas W. Chamberlain,
• E. Stephen Davies,
• Bradley E. Thomas,
• Martin Schröder and
• Andrei N. Khlobystov

Beilstein J. Org. Chem. 2014, 10, 332–343, doi:10.3762/bjoc.10.31

• m/z 791 and the solid state IR spectrum as a pressed disc in KBr indicated only one signal in the carbonyl region characteristic of the amide group (1653 cm−1) and no signal related to the carboxylic group stretch. The desired carboxylic acid compound [12] seems to be unstable under acidic

• other reagents and solvents were purchased from Aldrich and used without further purification. Compounds 1–3 and 7–10 were synthesised according to previously reported procedure [20]. Infra-red spectra were measured as KBr discs using a Nicolet Avatar 380 FTIR spectrometer over the range 400–4000 cm−1

• ), 70.85, 69.31, 60.22, 57.07 (sp3 carbons, 4 environments); MALDI–TOF MS (DCTB/MeCN, m/z): 1580.2 (M−); IR (KBr, ν, cm−1): 2960 (w), 2922 (w), 1645 (s), 1453 (w), 1328 (m), 1186 (m), 746 (m), 526 (s); UV–vis (CS2): λmax (ε × 10−3/dm3 mol−1 cm−1): 703 (0.750), 433 (8.526). Synthesis of 6 [70

Carbenoid-mediated nucleophilic “hydrolysis” of 2-(dichloromethylidene)-1,1,3,3-tetramethylindane with DMSO participation, affording access to one-sidedly overcrowded ketone and bromoalkene descendants^§

• Rudolf Knorr,
• Thomas Menke,
• Johannes Freudenreich and
• Claudio Pires

Beilstein J. Org. Chem. 2014, 10, 307–315, doi:10.3762/bjoc.10.28

• , assigned as above in accord with the deuterium-induced shifts 2Δ = –0.068 for C-2, 3Δ = −0.021 for C-3, and 3Δ = −0.045 ppm for C-1 as caused by the =CαD–S(O)–CD3 group incorporated during a run in [D6]DMSO; IR (KBr) ν: 2971, 2959, 2920, 2860, 1627 (w), 1484, 1363, 1032, 1022, 968, 748, 677, 505 cm−1; anal

• -CH3), 28.02 and 30.98 (2 × 1-/3-CH3), 47.17 (C-1/-3), 64.32 (C-2), 122.34 (C-4/-7), 127.12 (C-5/-6), 128.28 and 129.34 (2 × C-m and 2 × C-o), 138.36 (C-ipso), 143.50 (C-p), 149.99 (C-3a/7a), 201.25 (C=O) ppm; IR (KBr) ν: 2967, 2925, 2862, 1664 (s), 1606, 1480, 1368, 1228, 1209, 1186, 869, 759 cm−1

• /7a), 171.73 (2 × CO2H) ppm, assigned through comparison with the acid 10; IR (KBr) ν: 3400–2500 (very broad H–O), 1713 (s), 1291, 759 cm−1; anal. calcd for C15H18O4 (262.3): C, 68.69; H, 6.92; found: C, 69.23; H, 6.81. 40 was not formed from acid 10 with lithium N,N-diisopropylamide in THF as the

Secondary amine-initiated three-component synthesis of 3,4-dihydropyrimidinones and thiones involving alkynes, aldehydes and thiourea/urea

• Jie-Ping Wan,
• Yunfang Lin,
• Kaikai Hu and
• Yunyun Liu

Beilstein J. Org. Chem. 2014, 10, 287–292, doi:10.3762/bjoc.10.25

• with an X-4A instrument without correcting the temperature, IR spectra were measured in KBr on a Spectrum One apparatus and the HRMS were obtained under ESI mode in a Bruker 7-tesla FT-ICR MS instrument. General procedure for the three-component synthesis of DHPMs 5 Aldehyde 1 (0.3 mmol), urea/thiourea