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Vol. 26 No. 23 (2014)

Copyright (c) 2014 S. Shashidhar Reddy1, B. George Vineel1, S. Venkataiah1, A. Naidu2, P.K. Dubey2

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Synthesis of Novel (S)-Imidazolo[1,2c][1,2,3]triazolo-[4,5e]pyrimidine Derivatives

https://doi.org/10.14233/ajchem.2014.17565
S. Shashidhar Reddy1
1CiVentiChem (India) Private Limited, Plot No-72/A, Part-2, Phase-1, IDA Jeedimetla, Hyderabad-500 055, India 2Department of Chemistry, Jawaharlal Nehru Technological University University, Kukatpally, Hyderabad-500 085, India *Corresponding author: E-mail: shagum09@gmail.com
B. George Vineel1
1CiVentiChem (India) Private Limited, Plot No-72/A, Part-2, Phase-1, IDA Jeedimetla, Hyderabad-500 055, India 2Department of Chemistry, Jawaharlal Nehru Technological University University, Kukatpally, Hyderabad-500 085, India *Corresponding author: E-mail: shagum09@gmail.com
S. Venkataiah1
1CiVentiChem (India) Private Limited, Plot No-72/A, Part-2, Phase-1, IDA Jeedimetla, Hyderabad-500 055, India 2Department of Chemistry, Jawaharlal Nehru Technological University University, Kukatpally, Hyderabad-500 085, India *Corresponding author: E-mail: shagum09@gmail.com
A. Naidu2
1CiVentiChem (India) Private Limited, Plot No-72/A, Part-2, Phase-1, IDA Jeedimetla, Hyderabad-500 055, India 2Department of Chemistry, Jawaharlal Nehru Technological University University, Kukatpally, Hyderabad-500 085, India *Corresponding author: E-mail: shagum09@gmail.com
P.K. Dubey2
1CiVentiChem (India) Private Limited, Plot No-72/A, Part-2, Phase-1, IDA Jeedimetla, Hyderabad-500 055, India 2Department of Chemistry, Jawaharlal Nehru Technological University University, Kukatpally, Hyderabad-500 085, India *Corresponding author: E-mail: shagum09@gmail.com

Corresponding Author(s) : S. Shashidhar Reddy1

Asian Journal of Chemistry, Vol. 26 No. 23 (2014)

Abstract

Isopropyl azide (1) was reacted with cyanoacetamide (2) in the presence of sodium ethoxide to obtain 4-amino-3-isopropyl-3H-[1,2,3]triazolo-5-carboxamide (3) which on treatment with excess of diethyl carbonate and sodium ethoxide gave 3-isopropyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7-diol (4). The latter on treatment with POCl3 and 2,6-lutidine in the presence of catalytic amount of PCl5 resulted in 5,7-dichloro-3-isopropyl-3H-[1,2,3]triazolo[4,5-d] pyrimidine (5) in good yields. Compound 5 on condensation with L-prolinol (6) in ethanol yielded (S)-[1-(5-chloro-3-isopropyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine-7-yl)pyrrolidine-2-yl-methanol (7). Compound 7 on treatment with anilines (8a-8j) gave (S)-(1-(3-isopropyl-5-(arylamino)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-7-yl)pyrrolidine-2-yl) methanol (9a-j) by the nucleophilic displacement of the chlorine at 5th-position. 9a-j on treatment with POCl3 afforded a series of novel chiral derivatives of (S)-N-(3-isopropyl-7a,8,9,10[1'2':3,4]imidazolo[1,2c][1,2,3]triazolo[4,5e]pyrimidine5(7H)yl-idine) aniline hydrochloride (10a-j) by dehydrative cyclization. This cyclization also takes place with SOCl2 under refluxing conditions, but yields are low compared to the POCl3 conditions.

Keywords

Isopropylazide Cyanoacetamide L-Prolinol Triazole Triazolopyrimidine.
Shashidhar Reddy1, S., George Vineel1, B., Venkataiah1, S., Naidu2, A., & Dubey2, P. (2014). Synthesis of Novel (S)-Imidazolo[1,2c][1,2,3]triazolo-[4,5e]pyrimidine Derivatives. Asian Journal of Chemistry, 26(23), 8110–8114. https://doi.org/10.14233/ajchem.2014.17565
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