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A facile synthesis of substituted perhydro-1,3-thiazin-4-ones and 2-thioxoperhydro-4-pyrimidinones

✍ Scribed by Elghandour, Ahmed Hafez Hussien ;Ramiz, Mahmound Mohamed Mahfouz ;Ghozlan, Said Ahmed Soliman ;Elmoghayar, Mohamed Riffat Hamza

Publisher: John Wiley and Sons
Year: 1988
Tongue: English
Weight: 419 KB
Volume: 1988
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.198819881009

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✦ Synopsis

Depending on the reaction conditions eithcr 2.6-disubstitutcd 2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones 4 or 1,6-disubstitutcd 2-thiouracils 5 are readily prepared by base-catalyzcd cyclization of N-propenoylthioureas 3. Compounds 5 could also bc obtained by Dimroth-type rearrangement of 1,3-thiazin-4-ones 4 under the same reaction conditions.

Acyl and aroyl isothiocyanates are versatile building units that have been extensively utilized in organic synthesis I ".

We have recently reported8' the synthesis of 2-thioxopcrhydro-4-pyrimidinones by cyclization of N-cinnamoylthiourea derivatives. In the following we report ii new. simple. and efficient method for cyclizing thioureas into either 1.

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