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A facile one-pot synthesis of thiazo[2′,3′:2,1] imidazo[4,5-b]pyrane; thiazo[2′,3′:2,1]imidazo [4,5,b]pyridine; imidazo[2,1-b]thiazole and 2-(2-amino-4-methylthiazol-5-yl)-1-bromo-1,2-ethanedione-1-arylhydrazones

✍ Scribed by Samia M. Sayed; Maghraby A. Selim; Mohamed A. Raslan; Mohamed A. Khalil

Publisher
John Wiley and Sons
Year
2000
Tongue
English
Weight
138 KB
Volume
11
Category
Article
ISSN
1042-7163

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One-pot synthesis of imidazo[1,2-b]pyraz
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Hydrazonoyl halides 4 react readily with either 3-amino-2,3-dihydro-6-methyl-2-thioxo-4(1H)-pyrimidinone 5 or 3-amino-6-methyl-2-methylthio-4(3H)-pyrimidinone 6 to form 6H-pyrimido [1,2-b][1,2,4,5]tetrazin-6-ones 9. The mechanism of the studied reactions is discussed.

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The novel and versatile cyanomethyl 2amino-4-methylthiazolyl ketone (5) was prepared by treatment of bromomethyl 2-amino-4-methyl thiazolyl ketone (4) with potassium cyanide. Reaction of 5 with heterocyclic diazonium salts 6a,b and 10 afforded the corresponding hydrazones 7a,b and 11, respectively.