A tandem approach to isoquinolines from 2-azido-3-arylacrylates and alpha-diazocarbonyl compounds.
2-Azido-3-arylacrylates react with alpha-diazocarbonyl compounds and triphenylphosphine to furnish isoquinolines in 60-92% yields. The tandem process involves a Wolff rearrangement, an aza-Wittig reaction, and an electrocyclic ring closure. The procedure is efficient, rapid, and general, and the substrates are readily available.
Yang
Yun-Yun
YY
Department of Chemistry, Zhejiang University, Hangzhou, China.
Shou
Wang-Ge
WG
Chen
Zheng-Bo
ZB
Hong
Deng
D
Wang
Yan-Guang
YG
D000179:Acrylates / Q000737:chemistry*; D003979:Diazonium Compounds / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000179:Acrylates; D003979:Diazonium Compounds; D007546:Isoquinolines