Jump to main content
Jump to site search

Issue 1, 2018
Previous Article Next Article

A novel approach to 5H-pyrazino[2,3-b]indoles via annulation of 3-diazoindolin-2-imines with 2H-azirines or 5-alkoxyisoxazoles under Rh(ii) catalysis

Author affiliations

Abstract

A novel one-step method for the preparation of 5H-pyrazino[2,3-b]indoles with different substitution patterns in all rings of the tricyclic system via the Rh2(OAc)4-catalyzed reaction of 2H-azirines with 3-diazoindolin-2-imines is reported. Alkyl 5H-pyrazino[2,3-b]indole-3-carboxylates were also prepared by a one-pot procedure from synthetic equivalents of alkyl 2H-azirine-2-carboxylates, 5-alkoxyisoxazoles. The reactions provide the first examples of the use of Rh(II) catalysis for intermolecular annulations with 2H-azirines and isoxazoles.

Graphical abstract: A novel approach to 5H-pyrazino[2,3-b]indoles via annulation of 3-diazoindolin-2-imines with 2H-azirines or 5-alkoxyisoxazoles under Rh(ii) catalysis

Back to tab navigation

Supplementary files

Article information


Submitted
26 Oct 2017
Accepted
29 Nov 2017
First published
30 Nov 2017

Org. Biomol. Chem., 2018,16, 38-42
Article type
Communication

A novel approach to 5H-pyrazino[2,3-b]indoles via annulation of 3-diazoindolin-2-imines with 2H-azirines or 5-alkoxyisoxazoles under Rh(II) catalysis

J. O. Ruvinskaya, N. V. Rostovskii, I. P. Filippov, A. F. Khlebnikov and M. S. Novikov, Org. Biomol. Chem., 2018, 16, 38
DOI: 10.1039/C7OB02637D

Social activity

Search articles by author

Spotlight

Advertisements