Ecofriendly synthesis of novel benzo-1,2,3-triazol-1-yl-(N-aryl)amidines and their conversion to guanidines

Synthetic Communications

Volumn 41, Issue 11, 2011, Pages 1593-1602

  Philip, Sophia K ^a   Rajasekharan, K N ^b  

^a Christian College   (India)

^b UNIVERSITY OF KERALA   (India)

Author keywords

Benzo 1,2,3 triazol 1 yl (N aryl)amidines; Guanidines; Microwave assisted synthesis

Indexed keywords

AMIDINE; BENZOTRIAZOLE DERIVATIVE; CYANAMIDE; GUANIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; MICROWAVE RADIATION; REACTION ANALYSIS; SYNTHESIS;

EID: 79955678476     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.488312     Document Type: Article

References (14)

1. Berlinck, R. G. S.; Burtoloso, A. C. B.; Kossuga, M. H. The chemistry and biology of organic guanidine derivatives. Natural Prod. Rep. 2008, 25, 919-954.
2. + channels. J. Med. Chem. 1998, 41, 3048-3061. (Pubitemid 28359941)
3. Cesnek, M.; Holy, A.; Masojidkova, M.; Zidek, Z. Synthesis of 9-alkyl and 9-heteroalkyl substituted 2-amino-6-guanidinopurines and their influence on the NO-production in microphages. Bioorg. Med. Chem. 2005, 13, 2917-2926. (Pubitemid 40387500)
4. Saczewski, F.; Balewski, L. Biological activities of guanidine compounds. Exp. Opin. Ther. Patents 2009, 19, 1417-1448.
5. Furin, G. G.; Gatilov, Y. V.; Bagryanskaya, I. Y.; Zhuchgov, E. L. Guanidine in the synthesis of perfluoroalkylpyrimidines and perfluoroalkyl-s- triazines. Rus. Chem. Bull. Intl. 2001, 50, 476-479. (Pubitemid 33394597)
6. Nie, A.; Wang, J.; Huang, Z. Microwave-assisted solution-phase parallel synthesis of 2,4,6-trisubstituted pyrimidines. J. Comb. Chem. 2006, 8, 646-648. (Pubitemid 44578617)
7. Chen, J.; Pattarawarapan, M.; Zhang, A. J.; Burgess, K. Solution- and solidphase syntheses of substituted guanidinocarboxylic acids. J. Comb. Chem. 2000, 2, 276-281.
8. Katritzky, A. R.; Rogovoy, B. V. Recent developments in guanylating agents. Arkivoc 2005, 4, 49-87. (Pubitemid 40397747)
9. Castillo-Melenez, J. A.; Golding, B. T. Optimisation of the synthesis of guanidines from amines via nitroguanidines using 3,5-dimethyl-N-nitro-1H- pyrazole-1-carboxamidine. Synthesis 2004, 1655-1663. (Pubitemid 38918130)
10. Solodenko, W.; Broker, P.; Messinger, J.; Schon, U.; Kirschning, A. Amidination of amines under microwave conditions using recyclable polymer-bound 1H-pyrazole-1-carboxamidine. Synthesis 2006, 461-466. (Pubitemid 43241457)
11. Katritzky, A. R.; Parris, R. L.; Allin, S. M.; Steel, P. J. Benzotriazole-1-carboxamidinium tosylate: An alternative method for the conversion of amines to guanidines. Synth. Commun. 1995, 25, 1173-1186.
12. Bruker. SABADS, SMART, SAINTPLUS, and SHELXTL; Bruker AXS Inc.: Madison, WI, 2003.
13. Sheldrick, G. M. SHELXL-97: Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Germany, 1997.
14. Spek, A. L. Single-crystal structure validation with the program PLATON. J. Appl. Cryst. 2003, 36, 7-13.