Facile synthesis of pyrazolo[1, 5-a]pyridopyrazin-one via Smiles rearrangement or direct cyclization. Issue 12 (25th March 2015)

• Record Type: Journal Article
• Authors: Xiao, Youxin; Zhang, Zhicheng; Chen, Yinbo; Shao, Xusheng; Li, Zhong; Xu, Xiaoyong
• Is Part Of: Tetrahedron. Volume 71:Issue 12(2015)
• Page Start: 1863
• Page End: 1868
• Publication Date: 2015-03-25
• Subjects: Smiles rearrangement -- Cyclization -- Pyrazolo[1, 5-a]pyridopyrazin-one; KRYCGQGKABIYRU-UHFFFAOYSA-N -- MTVCKPODMFWLDK-UHFFFAOYSA-N -- ZMFWVWFUKUZEKP-UHFFFAOYSA-N -- GADIWTBGHMKSPG-UHFFFAOYSA-N -- ODEOIJJYMBJUBB-UHFFFAOYSA-N -- IVFSRPJXJSJSFD-UHFFFAOYSA-N -- ONDSXOAYUHLOAE-UHFFFAOYSA-N -- ZVSZARFQGGJNBQ-UHFFFAOYSA-N -- BFNCLECBFKORKC-UHFFFAOYSA-N -- YVROWIJKFRFBFH-UHFFFAOYSA-N -- GKUJUCYATVXJLO-UHFFFAOYSA-N -- XGRNIQWWFQXYGV-UHFFFAOYSA-N -- YVROWIJKFRFBFH-UHFFFAOYSA-N -- FAXVZIKAIXOVJU-UHFFFAOYSA-N -- RMQMCSFOYRAHQB-UHFFFAOYSA-N -- QWJZFJKQPSIFEP-UHFFFAOYSA-N -- BFNCLECBFKORKC-UHFFFAOYSA-N -- FXLWXQJIPMSTRG-UHFFFAOYSA-N -- KCWJJQLXCYOZBX-UHFFFAOYSA-N -- XGRNIQWWFQXYGV-UHFFFAOYSA-N -- HKEAVVREENCPNF-UHFFFAOYSA-N -- LEFDQWPTBWGPCO-UHFFFAOYSA-N -- SHMCPQBMWOJNAU-UHFFFAOYSA-N -- PUEULTAILYJVFP-UHFFFAOYSA-N -- YRSGAISRAJUERO-UHFFFAOYSA-N -- LEFDQWPTBWGPCO-UHFFFAOYSA-N; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.01.059
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A facile access to pyrazolo[1, 5- a ]pyridopyrazin-one is presented via Smiles rearrangement or direct cyclization. The method allows the convenient construction of a novel biaryl lactam in moderate to excellent yields starting from easily available precursors (18 examples, 75–97% yield). When R is an aryl group, two regioisomeric products were obtained, Smiles rearrangement product and direct cyclization product, but when R is alkyl or benzyl, Smiles rearrangement product was afforded selectively. In order to prove the proposed mechanism, intermediate6k was trapped. Graphical abstract: