Easy access to triazoles, triazolopyrimidines, benzimidazoles and imidazoles from imidates

Zarguil, A.; Boukhris, Saı̈d; Souizi, Abdelaziz; Essassi, El Mokhtar

doi:10.1016/j.tetlet.2008.07.134

Cited by 33 publications

(16 citation statements)

References 15 publications

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“…[35][36][37][38] Scheme 4. It has been shown that in the case of methylhydrazine, reaction lead to the formation of two triazole isomers (4f' and 4f'' in 75/25 ratio).…”

Section: Scheme 2 Synthesis Of N-sulfonamide Imidates 3a-ementioning

confidence: 99%

Simple and Efficient Synthesis of Some Novel Triazoles Sulfonamides

Balti¹,

Hachicha²,

M'rabet³

2015

HETEROCYCLES

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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.

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“…[35][36][37][38] Scheme 4. It has been shown that in the case of methylhydrazine, reaction lead to the formation of two triazole isomers (4f' and 4f'' in 75/25 ratio).…”

Section: Scheme 2 Synthesis Of N-sulfonamide Imidates 3a-ementioning

confidence: 99%

Simple and Efficient Synthesis of Some Novel Triazoles Sulfonamides

Balti¹,

Hachicha²,

M'rabet³

2015

HETEROCYCLES

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“…Acyl hydrazones also are important starting reactants to construct the backbone of 1,2,4-triazole ring and have been paid large attention due to the easy operations and highly active reactivities [69][70][71].…”

Section: Acyl Hydrazonesmentioning

confidence: 99%

“…The mixture of phenylhydrazine 114 and N-cyanobenimidate 115, which was obtained by the reaction of inexpensive reagents aldehydes using cyanamide as nitrogen source and N-bromosuccinimide as oxidant, could proceed the cyclization of intermolecular C-N and C-O bonds by onepot synthesis to afford 1,3,5-trisubstituted triazole 116 (82%) (Scheme 46) [167]. This synthesis could be further extended to the preparation of aniline substituted 1,2,4-triazoles in yields of 67-90% [71]. This method is an efficient one-pot procedure with the mild cyclization reaction of hydrazines to produce l,2,4-triazole derivatives in good yields.…”

Section: Cyclizations Of Hydrazinesmentioning

confidence: 99%

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Zhang¹,

Damu²,

Cai³

et al. 2014

COC

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Heterocyclic 1,2,4-triazole derivatives possess unusually spacious potentiality as medicinal agents, agricultural chemicals, functional materials, ionic liquids, supramolecular catalysts as well as artificial enzymes and receptors for supramolecular recognition and biomimetic catalysis, and their various researches and developments have been being a quite rapidly developing and active highlight topic with an infinite space. Numerous efforts have been directed toward various types of possible applications of 1,2,4-triazole-based compounds and a lot of important progress has been made, especially their preparations have attracted increasing attention. This review systematically summarized the recent advances in the syntheses of 1,2,4-triazole derivatives, including: (1) Cyclizations to form triazole ring; (2) Transformations of heterocyclic compounds to construct triazole ring; (3) Substitutions on 1,2,4-triazole ring; (4) Structural modifications in side chains of 1,2,4-triazole ring. It was hoped that this review would be helpful for the design and development of highly efficient preparation of 1,2,4-triazole derivatives with various sorts and varieties of extensively potential applications in medicine, agriculture, chemistry, materials, supramolecular sciences and so on.

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“…The preparation and investigation of bioactive nitrogen, oxygen and sulfur containing heterocycles is one of our ongoing projects. We have already developed some procedures to gain access to diverse structures as benzodiazepines 19 , triazoles, triazolopyrimidines, benzimidazoles and imidazoles 20 .…”

Section: Introductionmentioning

confidence: 99%