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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Synthetic Protocol for Pyrido[2,3-c]pyridazine and Pyrido[3,2-e][1,2]oxazine Scaffolds via a [4 + 2] Cycloaddition Reaction

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 14, 2025

Here, we revealed a convenient synthetic protocol for unique pyrido[2,3-c]pyridazine and pyrido[3,2-e][1,2]oxazine scaffolds with excellent regioselectvity diastereoselectivity. The functionalized pyrido[2,3-c] pyridazines were successfully synthesized via Cs2CO3-promoted [4 + 2] cycloaddition reaction of α-halogenated N-tosylhydrazones or N-acylhydrazones 5,6-unsubstituted 1,4-dihydropyridines under mild conditions. Additionally, the similar base-promoted α-chlorogenated oximes afforded pyrido[3,2-e][1,2]oxazines in satisfactory yields. features this included conditions, broad substrate scopes, high functional group tolerance, significant atomic economy.

Language: Английский

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Access to Spiro-Quinazolines via an Acid-Catalyzed Ring-Opening of Isatins with N-Alkylureas

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 25, 2025

Herein, we report novel p-TSA·H2O-catalyzed ring-opening reactions of isatins with N-alkylureas, allowing access to spiro-quinazolines excellent substrate scope and good yields. Introducing N,N-dialkylureas, 2,4-thiazolidinedione, or rhodamine into the leads a distinct set three-component reactions, yielding innovative incorporating sulfur atoms. Notably, protocol achieves superior level atomic economy, water as sole byproduct.

Language: Английский

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Selective Synthesis of Dihydro- and Dehydrogenated Spirocyclopenta[b]indoles via Acid-modulated [3+2] Cycloaddition Reaction

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: unknown, P. 140792 - 140792

Published: Nov. 1, 2024

Language: Английский

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