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Article: Cascade Cross-Coupling/Spirocyclization/Formal [4+2] Cycloaddition Reactions of 3-(2-Isocyanoethyl)Indoles with Aromatic Azides: Access to Polycyclic Spiroindolines Bearing A Pentasubstituted Guanidine Moiety

TitleCascade Cross-Coupling/Spirocyclization/Formal [4+2] Cycloaddition Reactions of 3-(2-Isocyanoethyl)Indoles with Aromatic Azides: Access to Polycyclic Spiroindolines Bearing A Pentasubstituted Guanidine Moiety
Authors
Gu, MZDeng, YQZhang, XTLin, XTXu, YBHu, XWLiu, XNZheng, YLChen, GSLiu, YL
Keywords3-(2-isocyanoethyl)indoles
aromatic azides
cross-coupling
polycyclic spiroindolines
spirocyclization
Issue Date20-Dec-2022
PublisherWiley
Citation
Advanced Synthesis & Catalysis, 2022, v. 364, n. 24, p. 4427-4432 How to Cite?
DOI: http://dx.doi.org/10.1002/adsc.202201168
Abstract

A rhodium-catalyzed cascade cross-coupling/spirocyclization/formal [4+2] cycloaddition reaction of 3-(2-isocyanoethyl)indoles with aromatic azides is developed, providing a general synthetic protocol to polycyclic spiroindolines bearing a pentasubstituted guanidine moiety with moderate to excellent yields. This transformation is highly effective since one C−C, one C=N, three C−N bonds as well as two new rings are constructed in a single step. More importantly, this work represents a new reactivity pattern of 3-(2-isocyanoethyl)indole, and thus constitutes an valuable addition to 3-(2-isocyanoethyl)indole chemistry.


Persistent Identifierhttp://hdl.handle.net/10722/357088
ISSN
1615-4150
2023 Impact Factor: 4.4
2023 SCImago Journal Rankings: 1.020
ISI Accession Number ID
WOS:000894055200001

 

DC FieldValueLanguage
dc.contributor.authorGu, MZ-
dc.contributor.authorDeng, YQ-
dc.contributor.authorZhang, XT-
dc.contributor.authorLin, XT-
dc.contributor.authorXu, YB-
dc.contributor.authorHu, XW-
dc.contributor.authorLiu, XN-
dc.contributor.authorZheng, YL-
dc.contributor.authorChen, GS-
dc.contributor.authorLiu, YL-
dc.date.accessioned2025-06-23T08:53:18Z-
dc.date.available2025-06-23T08:53:18Z-
dc.date.issued2022-12-20-
dc.identifier.citationAdvanced Synthesis & Catalysis, 2022, v. 364, n. 24, p. 4427-4432-
dc.identifier.issn1615-4150-
dc.identifier.urihttp://hdl.handle.net/10722/357088-
dc.description.abstract<p>A rhodium-catalyzed cascade cross-coupling/spirocyclization/formal [4+2] cycloaddition reaction of 3-(2-isocyanoethyl)indoles with aromatic azides is developed, providing a general synthetic protocol to polycyclic spiroindolines bearing a pentasubstituted guanidine moiety with moderate to excellent yields. This transformation is highly effective since one C−C, one C=N, three C−N bonds as well as two new rings are constructed in a single step. More importantly, this work represents a new reactivity pattern of 3-(2-isocyanoethyl)indole, and thus constitutes an valuable addition to 3-(2-isocyanoethyl)indole chemistry.</p>-
dc.languageeng-
dc.publisherWiley-
dc.relation.ispartofAdvanced Synthesis & Catalysis-
dc.rightsThis work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.-
dc.subject3-(2-isocyanoethyl)indoles-
dc.subjectaromatic azides-
dc.subjectcross-coupling-
dc.subjectpolycyclic spiroindolines-
dc.subjectspirocyclization-
dc.titleCascade Cross-Coupling/Spirocyclization/Formal [4+2] Cycloaddition Reactions of 3-(2-Isocyanoethyl)Indoles with Aromatic Azides: Access to Polycyclic Spiroindolines Bearing A Pentasubstituted Guanidine Moiety-
dc.typeArticle-
dc.identifier.doi10.1002/adsc.202201168-
dc.identifier.scopuseid_2-s2.0-85143522955-
dc.identifier.volume364-
dc.identifier.issue24-
dc.identifier.spage4427-
dc.identifier.epage4432-
dc.identifier.eissn1615-4169-
dc.identifier.isiWOS:000894055200001-
dc.identifier.issnl1615-4150-

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