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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

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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

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Publication details

The article was received on 26 Oct 2017, accepted on 29 Nov 2017 and first published on 30 Nov 2017


Article type: Communication
DOI: 10.1039/C7OB02637D
Citation: Org. Biomol. Chem., 2018, Advance Article
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    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, Advance Article , DOI: 10.1039/C7OB02637D

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