International Journal of Organic Chemistry

Volume 2, Issue 2 (June 2012)

ISSN Print: 2161-4687   ISSN Online: 2161-4695

Google-based Impact Factor: 1.26  Citations  

An Efficient and Convenient Synthesis of Certain 2-Thioxothiazole,2-oxo-1,2-dihydropridine, 2-Oxo-2H-pyran,2,4-diaminothiophene and Pyrazolo[5,1-c][1,2,4]triazine Derivatives Containing Antipyrine Moiety

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DOI: 10.4236/ijoc.2012.22021    5,115 Downloads   9,579 Views  Citations

ABSTRACT

2-Thioxothiazole derivatives 5a-c were prepared by reacting a mixture of 1a-c, CS2/KOH and 4-(2-chloroacetyl)-1, 5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one(3). Reacting 2-cyano-N-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-2H- pyrazol-4-yl)-2-thioxothiazol-3(2H)-yl)acetamide (5c) with mercaptoacetic acid, arylidenemalononitriles 8 and (E)- 3-(dimethylamino)-1-(furan-2-yl)prop-2-en-1-one (12) give 4-oxo-4,5-dihydrothiazole 6, 2-oxo-1,2-dihydropyridine 10 and 2-oxo-2H-pyran 15 respectively. Heating a mixture of 5c, malononitrile and elemental sulfur yield 2,4-diaminothio- phene 19. Coupling of 5c with the diazotized aminopyrazole 20 and aryldiazonium salts 23 give pyrazolo[5,1-c][1,2,4] triazines 22 and arylhydrazones 25 respectively.

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Ayyad, S. , El-Taweel, F. , Elagamey, A. and El-Mashad, T. (2012) An Efficient and Convenient Synthesis of Certain 2-Thioxothiazole,2-oxo-1,2-dihydropridine, 2-Oxo-2H-pyran,2,4-diaminothiophene and Pyrazolo[5,1-c][1,2,4]triazine Derivatives Containing Antipyrine Moiety. International Journal of Organic Chemistry, 2, 135-142. doi: 10.4236/ijoc.2012.22021.

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