Synthesis of pyrroloquinolines from substituted 6-aminoindoles and oxaloacetic ester

Content Provider	Semantic Scholar
Author	Yamashkin, S. A. Zhukova, Natalia V. Romanova, I. S.
Copyright Year	2008
Abstract	It was established that the initial condensation of substituted 6-aminoindoles and oxaloacetic ester in boiling benzene with the addition of catalytic amounts of acetic acid takes place exclusively through the carboxyl group of the keto ester with the formation of the corresponding enamines, which successfully undergo thermal cyclization (biphenyl, 280°C) to pyrroloquinolines. Here, irrespective of the nature of substituents at the N-1 and C-5 atoms enamines with a free position 7 are transformed into pyrrolo-[2,3-f]quinolines (structural analogs of vitamin PQQ) while 7-OMe-substituted enamines give pyrrolo[3,2-g]quinolines with linear fusion of the rings.
Starting Page	793
Ending Page	801
Page Count	9
File Format	PDF HTM / HTML
DOI	10.1007/s10593-008-0111-8
Volume Number	44
Alternate Webpage(s)	https://page-one.springer.com/pdf/preview/10.1007/s10593-008-0111-8
Alternate Webpage(s)	https://doi.org/10.1007/s10593-008-0111-8
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article