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Klásek A, Mrkvicka V, Pevec A, et al. Novel tandem hydration/cyclodehydration of alpha-thiocyanatoketones to 2-oxo-3-thiazolines. Application to thiazolo[5,4-c]quinoline-2,4(3aH,5H)-dione synthesis. J Org Chem. 2004;69(17):5646-51doi: 10.1021/jo0493370.
Klásek, A., Mrkvicka, V., Pevec, A., & Kosmrlj, J. (2004). Novel tandem hydration/cyclodehydration of alpha-thiocyanatoketones to 2-oxo-3-thiazolines. Application to thiazolo[5,4-c]quinoline-2,4(3aH,5H)-dione synthesis. The Journal of organic chemistry, 69(17), 5646-51. https://doi.org/10.1021/jo0493370
Klásek, Antonín, et al. "Novel tandem hydration/cyclodehydration of alpha-thiocyanatoketones to 2-oxo-3-thiazolines. Application to thiazolo[5,4-c]quinoline-2,4(3aH,5H)-dione synthesis." The Journal of organic chemistry vol. 69,17 (2004): 5646-51. doi: https://doi.org/10.1021/jo0493370
Klásek A, Mrkvicka V, Pevec A, Kosmrlj J. Novel tandem hydration/cyclodehydration of alpha-thiocyanatoketones to 2-oxo-3-thiazolines. Application to thiazolo[5,4-c]quinoline-2,4(3aH,5H)-dione synthesis. J Org Chem. 2004 Aug 20;69(17):5646-51. doi: 10.1021/jo0493370. PMID: 15307735.
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J Org Chem. 2004 Aug 20;69(17):5646-51. doi: 10.1021/jo0493370.

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

The Journal of organic chemistry

Antonín Klásek, Vladimír Mrkvicka, Andrej Pevec, Janez Kosmrlj

Affiliations

  1. Department of Food Engineering and Chemistry, Faculty of Technology, Tomas Bata University, CZ-762 72 Zlín, Czech Republic. [email protected]

PMID: 15307735 DOI: 10.1021/jo0493370

Abstract

Novel tandem hydration of alpha-thiocyanatoketones to thiocarbamates followed by in situ cyclodehydration to fused 2-oxo-3-thiazolines is described. The reaction is applied to the synthesis of [1,3]thiazolo[5,4-c]quinoline-2,4(3aH,5H)-diones (4). Concentrated sulfuric acid was found to be critical for the reaction as both corresponding 2,3-dioxo-1,2,3,4-tetrahydroquinolin-3-yl thiocyanates (2) and S-(2,4-dioxo-1,2,3,4-tetrahydroquinolin-3-yl) thiocarbamates (3) rapidly hydrolyze in the presence of water to 4-hydroxyquinolin-2(1H)-ones (1).

Copyright 2004 American Chemical Society

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