Base-Promoted Ring Contraction of Dihydrodiazepinones to Pyrrolinones

Anatoly Shutalev; Anastasia Fesenko

doi:10.3390/ecsoc-18-a024

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Base-Promoted Ring Contraction of Dihydrodiazepinones to Pyrrolinones

Anatoly Shutalev

^*,

Anastasia Fesenko

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

Published: 31 October 2014 by MDPI in The 18th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-18-a024

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

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Anatoly Shutalev

Anastasia Fesenko