Abstract
1,2,3-Triazolo[4,5-b]pyridines and pyrazolo[4,3-b]pyridines can be readily prepared via cyanoacetylation reactions of 5-amino-1,2,3-triazoles 1a,b and 4-amino- pyrazole 2 followed by subsequent cyclization of the formed cyanoacetamides. Reactions of amines 1a,b with a mixture of p-nitrophenylacetic acid and acetic anhydride under microwave irradiation conditions afforded the corresponding amides 15a,b that underwent cyclization to form 1,2,3-triazolo[4,5-b]pyridines 16a,b upon heating in DMF solutions containing sodium acetate. Reactions of 1a,b with active methylene compounds, including 17a-c, in the presence of zeolites as catalyst also afforded 1,2,3-triazolo[4,5-b]pyridine derivatives 20a-f via the intermediacy of triazole derivatives 19 and not 18.
Highlights
Pyrazolo[4,3-b]pyridine and triazolo[4,5-b]pyridine derivatives are of interest for their various applications as vasodilators, hypotensive, hypoglycemic, anti-inflammatory, analgesic, antiasthmatic, Molecules 2011, 16 antipyretic agents and as substrates of NAD glycohydrolase [1,2,3]
The present study describes the results of an investigation aimed at the preparation of a new class of 1,2,3-triazolo[4,5-b]pyridine and pyrazolo[4,3b]pyridine derivatives
Cyanoacetylation of o-acyl heteroarmatic amines is expected to give cyanoacetamides in which an active methylene moiety is located in close proximity to a ketone carbonyl function
Summary
Pyrazolo[4,3-b]pyridine and triazolo[4,5-b]pyridine derivatives are of interest for their various applications as vasodilators, hypotensive, hypoglycemic, anti-inflammatory, analgesic, antiasthmatic, Molecules 2011, 16 antipyretic agents and as substrates of NAD glycohydrolase [1,2,3]. Owing to these interesting biological activities and medicinal properties these azolopyridine derivatives have been the targets of investigations by several research groups [4,5,6,7,8]. We describe the results of an investigation of the preparation of cyanoacetamides and arylacetamides of 5-amino-1,2,3-triazoles and 4-aminopyrazoles and their utility in the preparation of condensed pyridines
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