One-step synthesis of the tricyclic core of martinellic acid from 2-(cyanomethyl)-3-oxo-N-arylbutanamides.
A SnCl4.5H2O-mediated facile and efficient one-step synthesis of the tricyclic core of martinellic acid from readily available 2-(cyanomethyl)-3-oxo-N-arylbutanamides was developed and a mechanism involving consecutive hydrolysis of a cyano group and a double annulation process is proposed.
Zhang
Zhiguo
Z
Department of Chemistry, Northeast Normal University, Changchun 130024, China.
Zhang
Qian
Q
Yan
Zihong
Z
Liu
Qun
Q
D000577:Amides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008958:Models, Molecular; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D012015:Reference Standards; D013237:Stereoisomerism
D000577:Amides; D011758:Pyrroles; D011804:Quinolines; C432345:martinellic acid