Stereoselective Synthesis of 12-Tetrazolyl Substituted (E)-5 H-Quinazolino[3,2- a]quinazolines via Sequential Ugi-Azide/Staudinger/aza-Wittig/Addition/Ag(I)-Catalyzed Cyclization

Mao-Lin Yang; Long Zhao; Hao-Ran Chen; Ming-Wu Ding

doi:10.1021/acs.joc.2c02621

Stereoselective Synthesis of 12-Tetrazolyl Substituted (E)-5 H-Quinazolino[3,2- a]quinazolines via Sequential Ugi-Azide/Staudinger/aza-Wittig/Addition/Ag(I)-Catalyzed Cyclization

J Org Chem. 2023 Feb 3;88(3):1898-1906. doi: 10.1021/acs.joc.2c02621. Epub 2023 Jan 17.

Authors

Mao-Lin Yang¹, Long Zhao¹, Hao-Ran Chen¹, Ming-Wu Ding¹

Affiliation

¹ Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Central China Normal University, Wuhan 430079, P. R. China.

PMID: 36649062
DOI: 10.1021/acs.joc.2c02621

Abstract

A new efficient and stereoselective synthesis of 12-tetrazolyl substituted (E)-5H-quinazolino[3,2-a]quinazolines via sequential Ugi-azide/Staudinger/aza-Wittig/addition/Ag(I)-catalyzed cyclization was developed. The four-component reactions of 2-azidobenzaldehyde, 2-(alkynyl)benzenamine, isocyanide, and trimethylsilyl azide gave Ugi-azide intermediates, which were subsequently treated with triphenylphosphine and isocyanate to produce 12-tetrazolyl substituted (E)-5H-quinazolino[3,2-a]quinazolines in the presence of Ag(I) catalyst and K₂CO₃.