Simple and Efficient Synthesis of Some Novel Triazoles Sulfonamides

Abstract

Reaction of iminoesters 1 with sulfonyl isocyanates gave the corresponding sulfonamide imidates 2. The cyclocondensation of the latter with a series of hydrazine in methanol affords new functionalized triazoles in high yields. Simple nitrogen-containing heterocycles attached to sulfonamido moieties have received a large amount of attention in the literature, as a consequence of their exciting biological properties and their role as pharmacophores of considerable historical importance. Heterocyclic sulfonamides are used as carbonic anhydrase inhibitors, 1-3 antibacterial agents, 4 anticancer, anti-inflammatory and analgesic agents, 5 β3adrenergic receptor agonists, 6 PC-1 inhibitors, 7 antifungal agents, 8 and antiviral agents. 9 Triazole derivatives have consistently attracted scientific and practical interest because of their widely varying chemical properties, synthetic versatility, and pharmacological activities, such as antibacterial, 10-12 antifungal, 13-15 antitubercular, 16-18 analgesic, 19,20 anti-inflammatory, 20-22 anticancer, 23,24 anticonvulsant, 25 antiviral, 26 insecticidal, 27 and antidepressant, 28 antiviral properties. Moreover, the triazole compounds carrying sulfone moiety have been reported as antibacterial and antifungal, antihypertensive, analgesic, anti-inflammatory, or antitumoral agents. 29-31 For these vast biological activities and in continuation of our work on the synthesis of novel nitrogen heterocyclic compounds containing a sulfamide group, 32 we undertook the synthesis of a new series of compounds incorporating the abovementioned biologically active moieties in one molecule. The scheme 1 depicts the discovery of a practical and high yielding method for the efficient one-pot synthesis of diverse triazole sulfonamides starting from a wide range of imidates.