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Issue 84, 2020
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Synthesis of β- and γ-lactam fused dihydropyrazinones from Ugi adducts via a sequential ring construction strategy

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Abstract

A modular approach for the construction of β- and γ-lactam fused dihydropyrazinones from the readily available Ugi adducts has been described. The sequential construction of rings through base-mediated cycloisomerization followed by acid-mediated cyclization yielded β-lactam fused dihydropyrazinones. However, the Ugi-derived dihydropyrazinones afforded γ-lactam fused dihydropyrazinones under base-mediated cycloisomerization. The regioselectivity in the cycloisomerization reactions is explained on the basis of ring-strain. Substrate scope, limitations and mechanistic investigations through DFT-calculations have been explored.

Graphical abstract: Synthesis of β- and γ-lactam fused dihydropyrazinones from Ugi adducts via a sequential ring construction strategy

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Article information


Submitted
25 Jun 2020
Accepted
15 Sep 2020
First published
15 Sep 2020

Chem. Commun., 2020,56, 12789-12792
Article type
Communication

Synthesis of β- and γ-lactam fused dihydropyrazinones from Ugi adducts via a sequential ring construction strategy

S. P. Singh, S. Tripathi, A. Yadav, R. Kant, H. K. Srivastava and A. K. Srivastava, Chem. Commun., 2020, 56, 12789
DOI: 10.1039/D0CC04415F

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