Events The 18th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 18th International Electronic Conference on Synthetic Organic Chemistry

Published date

31 Oct, 2014

Citation

Anastasia Fesenko, Anatoly Shutalev, Base-Promoted Ring Contraction of Dihydrodiazepinones to Pyrrolinones, in Proceedings of The 18th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2014, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-18-a024

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Base-Promoted Ring Contraction of Dihydrodiazepinones to Pyrrolinones

Anatoly Shutalev ¹

Anastasia Fesenko ¹

1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., 119991 Moscow, Russian Federation

Abstract

A novel synthesis of 2,3-dihydro-1H-1,3-diazepin-2-ones based on thermal elimination of methanol from 4-methoxy-2,3,4,5-tetrahydro-1H-1,3-diazepin-2-ones has been developed. The prepared dihydrodiazepinones underwent a new rearrangement under basic conditions to give 3-(aminomethylene)-2,3-dihydro-1H-pyrrol-2-ones. Plausible mechanism for the rearrangement is proposed.

Keywords

1H-1,3-Diazepin-2-ones

ring contraction

2,3-dihydro-1H-pyrrol-2-ones

anti-aromaticity

Manuscript

Ring Contraction.pdf

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