Molecules 2011, 16(5), 3723-3739; doi:10.3390/molecules16053723
Article

Acylation of Heteroaromatic Amines: Facile and Efficient Synthesis of a New Class of 1,2,3-Triazolo[4,5-b]pyridine and Pyrazolo[4,3-b]pyridine Derivatives

1 Chemistry Department, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait 2 Chemistry Department, Faculty of Science, Fayoum University, Fayoum, A. R., Egypt
* Author to whom correspondence should be addressed.
Received: 14 March 2011; in revised form: 21 April 2011 / Accepted: 26 April 2011 / Published: 4 May 2011
(This article belongs to the Section Organic Synthesis)
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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.
Keywords: cyanoacetic acid; cyanoacetamides; triazolo[4,5-b]pyridine; pyrazolo[4,3-b]- pyridine; p-nitrophenylacetic acid; zeolite

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MDPI and ACS Style

Ibrahim, H.M.; Behbehani, H.; Makhseed, S.; Elnagdi, M.H. Acylation of Heteroaromatic Amines: Facile and Efficient Synthesis of a New Class of 1,2,3-Triazolo[4,5-b]pyridine and Pyrazolo[4,3-b]pyridine Derivatives. Molecules 2011, 16, 3723-3739.

AMA Style

Ibrahim HM, Behbehani H, Makhseed S, Elnagdi MH. Acylation of Heteroaromatic Amines: Facile and Efficient Synthesis of a New Class of 1,2,3-Triazolo[4,5-b]pyridine and Pyrazolo[4,3-b]pyridine Derivatives. Molecules. 2011; 16(5):3723-3739.

Chicago/Turabian Style

Ibrahim, Hamada Mohamed; Behbehani, Haider; Makhseed, Saad; Elnagdi, Mohamed H. 2011. "Acylation of Heteroaromatic Amines: Facile and Efficient Synthesis of a New Class of 1,2,3-Triazolo[4,5-b]pyridine and Pyrazolo[4,3-b]pyridine Derivatives." Molecules 16, no. 5: 3723-3739.

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