Solvent-free synthesis of 5-(aryl/alkyl)amino-1, 2, 4-triazines and α-arylamino-2, 2′-bipyridines with greener prospects12. Issue 16 (31st January 2017)

• Record Type: Journal Article
• Authors: Kopchuk, Dmitry S.; Chepchugov, Nikolay V.; Kovalev, Igor S.; Santra, Sougata; Rahman, Matiur; Giri, Kousik; Zyryanov, Grigory V.; Majee, Adinath; Charushin, Valery N.; Chupakhin, Oleg N.
• Is Part Of: RSC advances. Volume 7:Issue 16(2017)
• Page Start: 9610
• Page End: 9619
• Publication Date: 2017-01-31
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c6ra26305d
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : A convenient approach towards 5-(aryl/alkyl)amino-1, 2, 4-triazines and α-arylamino-2, 2′-bipyridines was developed following ipso -substitution of a cyano-group by amino groups and, finally, aza-Diels-Alder reaction with 1-morpholynocyclopentene. Abstract : A green and highly efficient method has been developed for the synthesis of 5-(aryl/alkyl)amino-1, 2, 4-triazines and α-arylamino-2, 2′-bipyridines according to the principles of atom economy. It has been performed by two consecutive solvent-free reaction pathways: the ipso -substitution of a cyano-group in 5-cyano-1, 2, 4-triazines and the aza-Diels-Alder reaction of the resulting 5-arylamino-1, 2, 4-triazines with 1-morpholinocyclopentene used as a dienophile. Solvent and catalyst-free conditions, operational simplicity, the compatibility with various functional groups, nonchromatographic purification technique, and high yields are the notable advantages of this procedure. The present methodology possesses a low E -factor.