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Synthesis and reactivity of cyanomethyl 2‐amino‐4‐methylthiazolyl ketone. A facile synthesis of novel pyrazolo(5,1‐c)1,2,4‐triazine, 1,2,4‐triazolo(5,1‐c)1,2,4‐triazine, 1,2,4‐triazino(4,3‐a)benzimidazole, pyridazine‐6‐imine and 6‐oxopyridazinone derivatives

Synthesis and reactivity of cyanomethyl 2‐amino‐4‐methylthiazolyl ketone. A facile synthesis of... The novel and versatile cyanomethyl 2‐amino‐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. Refluxing of the hydrazones in pyridine afforded the corresponding pyrazolo(5,1‐c)‐1,2,4‐triazine, 1,2,4‐triazolo(5,1‐c)‐1,2,4‐triazine, and 1,2,4‐triazolo(4,3‐a)benzimidazole derivatives 8a,b and 12, respectively, via intramolecular cyclization. Compound 5 coupled also with benzenediazonium chloride to afford the corresponding hydrazone 14, which is an excellent precursor for the synthesis of pyridazine‐6‐imine 17a and pyridazinone 17b. The pyridazine derivatives 17a,b were also prepared by an independent route, that is, the condensation with malononitriles and coupling with benzenediazonium chloride, followed by intramolecular cyclization. © 1999 John Wiley & Sons, Inc. Heteroatom Chem 10: 385–390, 1999 http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Heteroatom Chemistry Wiley

Synthesis and reactivity of cyanomethyl 2‐amino‐4‐methylthiazolyl ketone. A facile synthesis of novel pyrazolo(5,1‐c)1,2,4‐triazine, 1,2,4‐triazolo(5,1‐c)1,2,4‐triazine, 1,2,4‐triazino(4,3‐a)benzimidazole, pyridazine‐6‐imine and 6‐oxopyridazinone derivatives

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References (7)

Publisher
Wiley
Copyright
Copyright © 1999 John Wiley & Sons, Inc.
ISSN
1042-7163
eISSN
1098-1071
DOI
10.1002/(SICI)1098-1071(1999)10:5<385::AID-HC8>3.0.CO;2-O
Publisher site
See Article on Publisher Site

Abstract

The novel and versatile cyanomethyl 2‐amino‐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. Refluxing of the hydrazones in pyridine afforded the corresponding pyrazolo(5,1‐c)‐1,2,4‐triazine, 1,2,4‐triazolo(5,1‐c)‐1,2,4‐triazine, and 1,2,4‐triazolo(4,3‐a)benzimidazole derivatives 8a,b and 12, respectively, via intramolecular cyclization. Compound 5 coupled also with benzenediazonium chloride to afford the corresponding hydrazone 14, which is an excellent precursor for the synthesis of pyridazine‐6‐imine 17a and pyridazinone 17b. The pyridazine derivatives 17a,b were also prepared by an independent route, that is, the condensation with malononitriles and coupling with benzenediazonium chloride, followed by intramolecular cyclization. © 1999 John Wiley & Sons, Inc. Heteroatom Chem 10: 385–390, 1999

Journal

Heteroatom ChemistryWiley

Published: Jan 1, 1999

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