Modular and Stereoselective Approach to Highly Substituted Indole/Pyrrole-Fused Diazepanones

Wang, Shutao; Wang, Siyu; Song, Shaoli; Gao, Qiansong; Wen, Chunxi; Zhang, Zhuoqi; Zheng, Lianyou; Xiang, Jinbao

doi:10.1021/acs.joc.1c00303

Cited by 14 publications

(7 citation statements)

References 43 publications

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“…The intramolecular aza-Michael additions of indoles to form fused seven-membered N-containing polycycles has been recently reported. [72] The best results are obtained when K 2 CO 3 or K 3 PO 4 are used as bases. The cyclization proceeds smoothly in DMSO at room temperature for 10 (K 2 CO 3 ) or 3 (K 3 PO 4 ) hours in 80 or 91% yields, correspondingly.…”

Section: Indoles and Purinesmentioning

confidence: 99%

Weak Nucleophiles in the Aza‐Michael Reaction

Rulev

2023

Adv Synth Catal

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The 1,4‐conjugated addition of nitrogen centered nucleophiles to electron‐deficient alkenes is one of the most significant and widely used reactions in modern synthetic organic chemistry. To date, various protocols for the aza‐Michael reaction have been developed. However, these reports mainly focus on the use of strong Michael donors. In recent years, the conjugate addition of weak nitrogen nucleophiles to various Michael acceptors gained increasing popularity. Impressive progress in this area has been achieved by the use of more efficient catalyst systems. This review aims to provide a critical analysis of the results obtained in reactions of weak nucleophiles (azoles, pyrroles, indoles, carbamates, purines, amides, hydrazides, uraciles etc) with electron‐deficient alkenes which were reported over the past twelve years.

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Section: Indoles and Purinesmentioning

confidence: 99%

Weak Nucleophiles in the Aza‐Michael Reaction

Rulev

2023

Adv Synth Catal

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“…However, to attain increased biological activities toward various diseases, many fused pyrrole and pyrrolidine analogs have been reported [65,66]. Further, these medicinally potent fused analogs have been derived from synthetic routes and isolation [67][68][69][70]. Because of this, present review also focuses very potent fused pyrrole and pyrrolidine analogs.…”

Section: Fused Pyrrole As Drug Candidatementioning

confidence: 99%

Therapeutic potential of pyrrole and pyrrolidine analogs: an update

Basha¹,

Basavarajaiah²,

Shyamsunder³

2022

Mol Divers

102

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The chemistry of nitrogen-containing heterocyclic compound pyrrole and pyrrolidine has been a versatile field of study for a long time for its diverse biological and medicinal importance . Biomolecules such as chlorophyll, hemoglobin, myoglobin, and cytochrome are naturally occurring metal complexes of pyrrole. These metal complexes play a vital role in a living system like photosynthesis, oxygen carrier, as well storage, and redox cycling reactions. Apart from this, many medicinal drugs are derived from either pyrrole, pyrrolidine, or by its fused analogs. This review mainly focuses on the therapeutic potential of pyrrole, pyrrolidine, and its fused analogs, more specifically anticancer, anti-inflammatory, antiviral, and antituberculosis. Further, this review summarizes more recent reports on the pyrrole, pyrrolidine analogs, and their biological potential. Graphical Abstract

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“…However, the protocol was applied to only monosubstituted oxetanes, resulting in the formation of only single-stereogenic center-equipped products. In our ongoing effort to utilize epoxide building blocks for the construction of benzo-fused heterocycles and inspired by the abovementioned Kuduk’s work and a recent report on the synthesis of indole/pyrrole-fused 1,4-diazepanones via a one-pot process starting from 1 H -indole/pyrrole-2-carboxylic acids and Morita–Baylis–Hillman-derived allylamines (Scheme C), we became interested in developing a new approach to the pyrazino[1,2- a ]indol-1-one core. We speculated that base-mediated (4+2) annulation of indole-2-carboxamides 1 with 2,3-epoxy tosylates 2 would allow a direct efficient access to 3,4-dihydropyrazino[1,2- a ]indol-1(2 H )-ones 3 (Scheme D).…”

Section: Introductionmentioning

confidence: 99%

Base-Mediated, Chemo- and Regioselective (4+2) Annulation of Indole-2-carboxamides with 2,3-Epoxy Tosylates toward 1,2-Fused Indoles

Das

2023

J. Org. Chem.

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annulation of indole-2-carboxamides with 2,3-epoxy tosylates has been explored. The protocol delivers 3-substituted pyrazino[1,2-a]indol-1-ones in high yields in diastereoselective fashion, and neither 4-substituted pyrazino[1,2a]indol-1-ones nor tetrahydro-1H-[1,4]diazepino[1,2-a]indol-1-ones are generated, irrespective of whether the distal epoxide C3 substituent is alkyl or aryl, or the epoxide is cis-or trans-configured. This reaction proceeds in one pot via N-alkylation of the indole scaffold with 2,3-epoxy tosylates, concomitantly followed by 6-exo-selective epoxide-opening cyclization. Notably, the process is chemo-and regioselective with respect to both the starting materials. To our knowledge, the process represents the first successful example of one-pot annulation of indole-based diheteronucleophiles with epoxide-based dielectrophiles.

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Modular and Stereoselective Approach to Highly Substituted Indole/Pyrrole-Fused Diazepanones

Cited by 14 publications

References 43 publications

Weak Nucleophiles in the Aza‐Michael Reaction

Weak Nucleophiles in the Aza‐Michael Reaction

Therapeutic potential of pyrrole and pyrrolidine analogs: an update

Base-Mediated, Chemo- and Regioselective (4+2) Annulation of Indole-2-carboxamides with 2,3-Epoxy Tosylates toward 1,2-Fused Indoles

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