Novel tandem hydration/cyclodehydration of a-thiocyanatoketones to 2-oxo-3-thiazolines. Application to thiazolo[5,4-c]quinoline-2,4(3aH,5H)-dione synthesis.

Klásek, Antonín; Mrkvička, Vladimír; Pevec, Andrej; Košmrlj, Janez

Title:

Author:

Klásek, Antonín; Mrkvička, Vladimír; Pevec, Andrej; Košmrlj, Janez

Document type:

Peer-reviewed article (English)

Source document:

Journal of Organic Chemistry. 2004, vol. 69, issue 17, p. 5646-5661

ISSN:

0022-3263 (Sherpa/RoMEO, JCR)

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DOI:

https://doi.org/10.1021/jo0493370

Abstract:

Novel tandem hydration of a-thiocyanatoketones to thiocarbamates followed by in situ cyclodehydration to fused 2-oxo-3-thiazolines is described. Concentrated sulfuric acid was found to be critical for the reaction as both corresponding thiocyanates and thiocarbamates rapidly hydrolyze in the presence of water.

Full text:

http://pubs.acs.org/doi/full/10.1021/jo0493370

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Citace článku v časopise:
KLÁSEK, Antonín, Vladimír MRKVIČKA, Andrej PEVEC a Janez KOŠMRLJ. Novel tandem hydration/cyclodehydration of a-thiocyanatoketones to 2-oxo-3-thiazolines. Application to thiazolo[5,4-c]quinoline-2,4(3aH,5H)-dione synthesis. Journal of Organic Chemistry [online]. 2004, vol. 69, iss. 17, s. 5646-5661. [cit. 2024-11-21]. ISSN 0022-3263. Dostupné z: http://pubs.acs.org/doi/full/10.1021/jo0493370.

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