Events The 14th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session c. Microwave Assisted Synthesis of the event The 14th International Electronic Conference on Synthetic Organic Chemistry

Published date

25 Oct, 2010

Citation

A. P. Esteves, L. M. Rodrigues, J. C. O. Gonçalves, Ana M. F. Oliveira-Campos, Synthesis of 5H-pyrido[4,3-b]indole by a modification of Pomeranz-Fritsch isoquinoline synthesis, in Proceedings of The 14th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2010, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-14-00442

Facebook

Twitter

Synthesis of 5H-pyrido[4,3-b]indole by a modification of Pomeranz-Fritsch isoquinoline synthesis

A. P. Esteves ¹

L. M. Rodrigues ¹

J. C. O. Gonçalves ¹

Ana M. F. Oliveira-Campos ¹

1. Centro de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal

Abstract

5H-Pyrido[4,3-b]indole was obtained from 3-formylindole in 16% overall yield by Jackson and Shannon modification of the Pomeranz-Fristch isoquinoline synthesis. The final cyclisation occurred but the removal of the tosyl group and oxidation of the dihydrocompound was not efficient. Changes in the concentration of the acid catalyst gave 29% as the best yield for the last step. An NMR study of the cyclisation is described.

Keywords

pyrido[4,3-b]indole

γ-carboline

isoquinoline

Pomeranz-Fritsch

New thiosemicarbazones based on quinoline scaffold as anticancer iron chelators

The Increase of the 1,3-dinitrobenzoyleneurea Photochemical Reactivity in the Presence of the H-atom donors