Journal
CHEMICAL COMMUNICATIONS
Volume 56, Issue 84, Pages 12789-12792Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0cc04415f
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Funding
- SERB, New Delhi [CRG/2018/001897, SB/S2/RJN/004-2015]
- NIPER Guwahati
- Department of Chemistry, IIT Guwahati
- CSIR
- UGC
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A modular approach for the construction of beta- and gamma-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 beta-lactam fused dihydropyrazinones. However, the Ugi-derived dihydropyrazinones afforded gamma-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.
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