Direct access to pyrido/pyrrolo[2,1-b]quinazolin-9(1H)-ones through silver-mediated intramolecular alkyne hydroamination reactions

Hengshuai Wang; Shengchao Jiao; Kerong Chen; Xu Zhang; Linxiang Zhao; Dan Liu; Yu Zhou; Hong Liu

doi:10.3762/bjoc.11.47

Direct access to pyrido/pyrrolo[2,1-b]quinazolin-9(1H)-ones through silver-mediated intramolecular alkyne hydroamination reactions

Beilstein J Org Chem. 2015 Mar 30:11:416-24. doi: 10.3762/bjoc.11.47. eCollection 2015.

Authors

Hengshuai Wang¹, Shengchao Jiao², Kerong Chen¹, Xu Zhang¹, Linxiang Zhao³, Dan Liu³, Yu Zhou¹, Hong Liu¹

Affiliations

¹ CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, P. R. China.
² CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, P. R. China ; Shenyang Pharmaceutical University, 103 Wenhua Road, Shengyang 110016, P. R. China.
³ Shenyang Pharmaceutical University, 103 Wenhua Road, Shengyang 110016, P. R. China.

Abstract

We report a synthetic methodology for the construction of the fused heterocyclic compounds pyrido[2,1-b]quinazolin-9(1H)-ones and pyrrolo[2,1-b]quinazolin-9(1H)-ones through an AgOTf-catalyzed intramolecular alkyne hydroamination reaction. The methodology is applicable to a wide scope of substrates and produces a series of fused quinazolinone heterocycles in good to excellent yields.

Keywords: heterocyclic molecules; intramolecular alkyne hydroamination; silver.