Synthetic Routes to Isomeric Imidazoindoles by Regioselective Ring‐Opening of Activated Aziridines Followed by Copper‐Catalysed C–N Cyclization

Sayyad, Masthanvali ; Wani, Imtiyaz Ahmad ; Tiwari, Deo Prakash ; Ghorai, Manas K. (2017) Synthetic Routes to Isomeric Imidazoindoles by Regioselective Ring‐Opening of Activated Aziridines Followed by Copper‐Catalysed C–N Cyclization European Journal of Organic Chemistry, 2017 (16). pp. 2369-2378. ISSN 1434-193X

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Official URL: http://doi.org/10.1002/ejoc.201700267

Related URL: http://dx.doi.org/10.1002/ejoc.201700267

Abstract

Ring opening of activated aziridines with i) 2,2‐dibromovinylanilines and ii) 2‐bromoindoles followed by Cu‐catalysed cyclization gives rise to different regioisomers of imidazoindoles. The first route generates one regioisomer, and the second route gives the other. Two new synthetic routes that deliver substituted imidazoindoles in high yields with excellent ee values have been developed. The reactions proceed through ring‐opening of activated aziridines with 2,2‐dibromovinylanilines or 2‐bromoindoles, followed by a Cu‐catalysed domino C–N,C–N‐cyclization, or a C–N cyclization, respectively. The first route gives rise to one regioisomer, and the second route gives the other.

Item Type:Article
Source:Copyright of this article belongs to John Wiley & Sons, Inc.
Keywords:Aziridines; Small Ring Systems; Fused Ring Systems; Nitrogen Heterocycles; Copper; Cyclization.
ID Code:117094
Deposited On:15 Apr 2021 07:45
Last Modified:15 Apr 2021 07:45

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