EventsThe 26th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-26-13568
This submission belongs to the session S1. General Organic Synthesis of the event The 26th International Electronic Conference on Synthetic Organic Chemistry
Published date
14 Nov, 2022
Academic Editor
author-avatarJulio A. Seijas
Citation
Anatoly Shutalev, Anastasia A. Fesenko, An unexpected result of base-promoted rearrangement of 4a-acetyl-8a-hydroxydecahydroquinazoline-2-thione, in Proceedings of The 26th International Electronic Conference on Synthetic Organic Chemistry, 15 November–30 November 2022, MDPI: Basel, Switzerland, 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 1
Anastasia A. Fesenko 2
1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., 119991 Moscow, Russian Federation, Russia
2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., 119991 Moscow, Russian Federation
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
Manuscript
sciforum_066738_original_Manuscript_revised_Shutalev.pdf
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