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3 article(s) from Das, Sajal Kumar

Regioselectivity of the S_EAr-based cyclizations and S_EAr-terminated annulations of 3,5-unsubstituted, 4-substituted indoles

Jonali Das and
Sajal Kumar Das

Beilstein J. Org. Chem. 2022, 18, 293–302, doi:10.3762/bjoc.18.33

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Graphical Abstract

Scheme 1: S_EAr-based, C_Ar–C bond-forming cyclization or annulation of: (A) substituted arenes/heteroarenes an...

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Scheme 2: Indole C3 regioselective intramolecular alkylation of indolyl allyl carbonates.

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Scheme 3: Indole C3 regioselective Michael-type cyclization in the total synthesis of (−)-indolactam V.

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Scheme 4: Synthesis of azepino[4,3,2-cd]indoles via indole C3 regioselective aza-Michael addition/cyclization...

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Scheme 5: Indole C3 regioselective Pictet−Spengler reaction of 2-(1H-indol-4-yl)ethanamines.

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Scheme 6: Indole C3 regioselective hydroindolation of cis-β-(α′,α′-dimethyl)-4′-methindolylstyrenes.

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Scheme 7: Indole C3 regioselective cyclization leading to the formation of polycyclic azepino[5,4,3-cd]indole...

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Scheme 8: Synthesis of azepino[3,4,5-cd]indoles via iridium-catalyzed asymmetric [4 + 3] cycloaddition of rac...

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Scheme 9: Aldimine condensation/1,6-hydride transfer/Mannich-type cyclization cascade of indole-derived pheny...

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Scheme 10: Indole C5 regioselective intramolecular FC acylation of 4-substituted indoles.

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Scheme 11: Catalyst-dependent regioselectivity switching in the cyclization of ethyl 2-diazo-4-(4-indolyl)-3-o...

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Scheme 12: Indole C5 regioselective cyclization of α-carbonyl sulfoxonium ylides.

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Scheme 13: Indole C5 regioselective cyclization of an indole-tethered donor–acceptor cyclopropane.

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Scheme 14: Indole C5 regioselective epoxide–arene cyclization.

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Commentary

Published 08 Mar 2022

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Studies directed toward the exploitation of vicinal diols in the synthesis of (+)-nebivolol intermediates

Runjun Devi and
Sajal Kumar Das

Beilstein J. Org. Chem. 2017, 13, 571–578, doi:10.3762/bjoc.13.56

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Figure 1: The chroman-based antihypertensive drug nebivolol, its biologically active stereoisomers and late-s...

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Scheme 1: Synthetic strategies toward late-stage intermediates of 1a.

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Scheme 2: Attempted synthesis of (±)-2 via intramolecular S_NAr reaction.

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Scheme 3: Speculation on the synthesis of a 2-substituted chroman derivative based on Borhan’s approach.

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Scheme 4: Synthesis of syn-2,3-dihydroxy esters 19 and 20.

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Scheme 5: Attempted cyclization according to Borhan’s method.

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Scheme 6: Synthesis of β-hydroxy-α-tosyloxy esters 24 and 25.

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Scheme 7: Speculation of simultaneous epoxidation/epoxide-ring opening.

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Scheme 8: Synthesis of chroman diols 2 and 29, respectively.

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Scheme 9: Conversion of 32 into 3 via Mitsunobu inversion.

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Scheme 10: Synthesis of chroman epoxide 5.

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Letter

Published 21 Mar 2017

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cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin

Dimpee Gogoi,
Runjun Devi,
Pallab Pahari,
Bipul Sarma and
Sajal Kumar Das

Beilstein J. Org. Chem. 2016, 12, 2816–2822, doi:10.3762/bjoc.12.280

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Figure 1: Chroman-based tetracyclic natural products 1–4 of the brazilin family and our designed, B-ring-modi...

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Scheme 1: Retrosynthetic analysis of the designed B-ring-modified analogues of brazilin.

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Scheme 2: The synthetic challenge associated with the synthesis of 5 by IFCEA of 6 (above) and recent literat...

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Figure 2: Assessment of the IFCEA cyclization on additional substrates (±)-6b–n leading to (±)-5b–n. Reaction...

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Figure 3: ORTEP diagram of 5k.

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Scheme 3: Stereoselective conversion of (±)-5k into (±)-14.

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Letter

Published 21 Dec 2016

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Regioselectivity of the SEAr-based cyclizations and SEAr-terminated annulations of 3,5-unsubstituted, 4-substituted indoles

Studies directed toward the exploitation of vicinal diols in the synthesis of (+)-nebivolol intermediates

cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin

Regioselectivity of the S_EAr-based cyclizations and S_EAr-terminated annulations of 3,5-unsubstituted, 4-substituted indoles