An unexpected result of base-promoted rearrangement of 4a-acetyl-8a-hydroxydecahydroquinazoline-2-thione

Anatoly Shutalev; Anastasia Fesenko

doi:10.3390/ecsoc-26-13568

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An unexpected result of base-promoted rearrangement of 4a-acetyl-8a-hydroxydecahydroquinazoline-2-thione

Anatoly Shutalev

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Anastasia A. Fesenko

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

Academic Editor: Julio A. Seijas

Published: 14 November 2022 by MDPI in The 26th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-26-13568

Abstract:

Treatment of 4a-acetyl-8a-hydroxydecahydroquinazoline-2-thione with NaH in acetonitrile leads to its isomerization into 1-hydroxy-1-methyl-3-thioxo-2,4-diazaspiro[5.5]undecan-7-one followed by the C1-C6 bond cleavage to give N-acetyl-N¢-[(2-oxocyclohexyl)methyl]thiourea. The starting compound as a single diastereomer was prepared by the reaction between the K-enolate of 2-acetylcyclohexanone and N-(tosylmethyl)thiourea or N-(azidomethyl)thiourea.

Keywords: N-(azidomethyl)thiourea; N-(tosylmethyl)thiourea; 2-acetylcyclohexanone; 4a-acetyl-8a-hydroxydecahydroquinazoline-2-thione; rearrangement

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Anatoly Shutalev

Anastasia Fesenko