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Issue 11, 2017
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Catalyst-free [3 + 2] cyclization of imines and Morita–Baylis–Hillman carbonates: a general route to tetrahydropyrrolo[2,1-a]isoquinolines and dihydropyrrolo[2,1-a]isoquinolines

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Abstract

We have developed a mild and efficient catalyst-free [3 + 2] cyclization of isoquinoline imines and Morita–Baylis–Hillman carbonates. Various tetrahydropyrrolo[2,1-a]isoquinolines can be prepared in acceptable to excellent yields (up to 96%). The treatment of tetrahydropyrroloisoquinolines with DDQ afforded 5,6-dihydropyrrolo[2,1-a]isoquinolines in good yields (up to 90%). A one-pot synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines has been achieved successfully (up to 86% yield). It should be noted that all the [3 + 2] cyclization, oxidation and one-pot reactions can be easily scaled up to the gram scale.

Graphical abstract: Catalyst-free [3 + 2] cyclization of imines and Morita–Baylis–Hillman carbonates: a general route to tetrahydropyrrolo[2,1-a]isoquinolines and dihydropyrrolo[2,1-a]isoquinolines

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Article information


Submitted
20 Jun 2017
Accepted
24 Jul 2017
First published
24 Jul 2017

Org. Chem. Front., 2017,4, 2128-2133
Article type
Research Article

Catalyst-free [3 + 2] cyclization of imines and Morita–Baylis–Hillman carbonates: a general route to tetrahydropyrrolo[2,1-a]isoquinolines and dihydropyrrolo[2,1-a]isoquinolines

X. Tang, M. Yang, C. Ye, L. Liu, H. Zhou, X. Jiang, X. You, B. Han and H. Cui, Org. Chem. Front., 2017, 4, 2128
DOI: 10.1039/C7QO00492C

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