Azide‐Triggered Bicyclization of o‐Alkynylisocyanobenzenes: Synthesis of Tetrazolo[1, 5‐a]quinolines. Issue 42 (17th October 2019)

• Record Type: Journal Article
• Authors: Khaikate, Onnicha; Soorukram, Darunee; Leowanawat, Pawaret; Pohmakotr, Manat; Reutrakul, Vichai; Kuhakarn, Chutima
• Is Part Of: European journal of organic chemistry. Issue 42(2019)
• Page Start: 7050
• Page End: 7057
• Publication Date: 2019-10-17
• Subjects: Cyclization -- Isocyanides -- Nitrogen heterocycles -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201901209
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : An efficient and rapid synthetic approach for the synthesis of tetrazolo[1, 5‐ a ]quinolines has been developed employing the reaction of o ‐alkynylisocyanobenzenes with sodium azide. The present strategy involved nucleophilic addition of azide to isocyanide followed by 6‐ endo cyclization. The reaction gives access to a collection of tetrazolo[1, 5‐ a ]quinolines with broad functional group in moderate to high yields under metal‐, and base‐free conditions. Abstract : An efficient synthesis of tetrazolo[1, 5‐ a ]quinolines employing the reaction of o ‐alkynylisocyanobenzenes with sodium azide is described. The reaction proceeds through the nucleophilic addition of the azide to the isocyanide and a subsequent by 6‐endo cyclization.