Rapid construction of tricyclic tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine via isocyanide-based multicomponent reaction

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 1436 - 1443

Published: June 28, 2024

An efficient protocol for the synthesis of polyfunctionalized tetrahydrocyclopenta[4,5]pyrrolo[2,3- b ]pyridine-3,4b,5,6,7(1 H )-pentacarboxylates was developed by a three-component reaction. In absence any catalyst, reaction alkyl isocyanides, dialkyl but-2-ynedioates and 5,6-unsubstituted 1,4-dihydropyridines in refluxing acetonitrile afforded high yields with diastereoselectivity. The finished situ generation activated 5-(alkylimino)cyclopenta-1,3-dienes from addition isocyanide to two molecules sequential formal [3 + 2] cycloaddition 1,4-dihydropyridine.

Language: Английский

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Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10854 - 10866

Published: July 12, 2024

A convenient synthetic protocol for diverse fused chromenes was successfully developed by a three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and various cyclic 1,3-dipolarophiles containing

Language: Английский

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Construction of Spiro[indoline‐3,2′‐pyrrolo[2,1‐a]Isoquinoline] and Spiro[indoline‐3,2′‐pyrrolo[1,2‐a]Quinoline] via Isocyanide‐Based Three‐Component Reaction

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(4)

Published: Jan. 1, 2025

Abstract A convenient synthetic protocol for novel spiro[indoline‐3,2′‐pyrrolo[2,1‐ a ]isoquinoline] and spiro[indoline‐3,2′‐pyrrolo[1,2‐ ]quinoline] motifs was successfully developed by three‐component reaction of isoquinoline (quinoline), cyclohexyl isocyanide, isatylidene malononitriles. In the absence any catalyst, isoquinoline, malononitriles in refluxing dichloromethane gave functionalized ]isoquinolines] good yields with high diastereoselectivity. However, similar quinoline afforded ]quinolines] about 2:1

Language: Английский

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Advances in the synthesis of aryl-fused six- to nine-membered N,O-heterocycles

Russian Chemical Bulletin, Journal Year: 2025, Volume and Issue: 74(3), P. 585 - 622

Published: March 1, 2025

Language: Английский

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Using Triazolobenzodiazepine as the Cyclic Imine in Various Types of Joullié–Ugi Reactions

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(19), P. 13504 - 13519

Published: Sept. 11, 2023

The triazolobenzodiazepine as a cyclic imine was employed in variety of Joullié–Ugi reactions, and three new families unique connected to carboxamide tetrazole products were synthesized via three-component reaction the isocyanides with each species carboxylic acid/water/TMSN3 under mild conditions high yields. Furthermore, used an interesting strategy based on modified Ugi (pseudo-Joullié–Ugi reaction) imines isocyanide acetylenedicarboxylates catalyst-free for synthesis triazolobenzodiazepine-fused pyrroles. Mechanistic investigation reveals that pyrroles have been generated surprising route. Significantly, use Joullié–Ugi, azido-Joullié–Ugi, pseudo-Joullié–Ugi reactions broad scope biological scaffolds occurred mild, simple without any catalyst.

Language: Английский

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Recent Progress in Transformations of Azepine/Oxazepine/Thiazepine Derivatives

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(13)

Published: March 27, 2024

Abstract Dibenzoazepine, dibenzoxazepine and dibenzothiazepine scaffolds are an important class of N ‐heterocycles that possess multiple biological activities. Due to the widespread application these motifs in drug discovery, synthesis tri‐cyclic seven‐membered imines/amines has gained huge attention chemists. In present review, we have highlighted recent advances functionalization cyclization reactions valuable organic compounds over last six years.

Language: Английский

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Isocyanide-based multicomponent reactions for the synthesis of benzopyran derivatives with biological scaffolds

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(6), P. 1102 - 1134

Published: Jan. 1, 2024

The present review covers all isocyanide-based multicomponent reactions for the preparation of benzopyrans, which serve as parent cores many essential drugs, natural compounds, and biological compositions.

Language: Английский

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Synthesis of tetracyclic dibenzo[b,f][1,4]oxazepine-fused β-lactams via visible-light-induced Staudinger annulation

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(35), P. 7106 - 7114

Published: Jan. 1, 2023

An efficient visible-light-induced Staudinger [2 + 2] annulation reaction between α-diazo ketones and dibenzo[b,f][1,4]oxazepine/thiazepine-imines under catalyst-free conditions has been developed. This protocol provides a facile method to synthesize tetracyclic dibenzo[b,f][1,4]oxazepine/thiazepine-fused β-lactams bearing quaternary carbon center with broad substrate scope high efficiency (37 examples, up >99% yield).

Language: Английский

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Five-membered ring systems: Pyrroles and benzo analogs

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 123 - 173

Published: Jan. 1, 2024

Language: Английский

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Synthesis of pyrrole-fused dibenzoxazepine/dibenzothiazepine/triazolobenzodiazepine derivatives via isocyanide-based multicomponent reactions

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2870 - 2882

Published: Nov. 11, 2024

An efficient and facile synthesis of pyrrole-fused dibenzoxazepine/dibenzothiazepine/triazolobenzodiazepine derivatives was developed through the isocyanide-based multicomponent reaction isocyanides,

Language: Английский

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