Synthesis, Antibacterial, and Antifungal Activities of Imidazo[2,1-c][1,2,4]triazoles and 1,2,4-Triazolo[4,3-a]pyrimidinones

Abstract

Starting materials5-Amino-1-phenyl [1,2,4]triazole 1a-c were prepared from the corresponding cyanamide and hydrazonate phenyles according to literature [12] by gently refluxing in methanol. 5-Amino-3-methyl-1-phenyl[1,2,4]triazole 1a:This compound was obtained as yellow solid, 85% yield, mp 134 °C [Lit[12]mp 136 °C]; IR (cm -1 ): υ = 1537-1616(C=N), 3397-3477(NH 2 ); 1H NMR: δ (ppm) 2.33( s,

Synthesis of Novel Derivatives of Imidazo[2,1-c][1,2,4]Triazine from Biologically Active 4-Arylidene-2-Hydrazino-1-Phenyl-1H-Imidazol-5(4H)-Ones and Evaluation of their Antimicrobial Activity

“…one carbonyl band at 1718-1700 cm -1 . In addition, the 1 H NMR spectrum showed the signal of =CH triazine at 6.35-6.90 ppm and one D 2 O exchangeable signal for NH at 9.10-11.14 ppm, indicating the appropriate structure of 4a-n. 27,28 6 -Arylidine-3-methyl-8-phenylimidazo [2,1-c][1,2,4] triazine-4,7(6H,8H)diones 7a-c were prepared through heating compounds 6a-c with pyruvic acid in an oil bath for 1 h. 29 Compounds 7a-c were characterised using elemental analysis as well as spectroscopic analysis. IR spectra showed the absence of the NH 2 bands of the hydrazine moiety and the appearance of two bands at 1739-1705 cm -1 and 1650-1645 cm -1 representing two carbonyl bands instead of just one band in compounds 6a-c.…”

A Multifield Study on Dimethyl Acetylenedicarboxylate: A Reagent Able to Build a New Cycle on Diaminoimidazoles

“…In a first step, an addition ofDMAD at the multiple bond by the amino or mercapto group of the starting triazole occurs, then an intramolecular cyclization on the NH fragment due to the “far” ester group happens. A similar process, involving N -substituted aminotriazoles 6 , [ 25 ] aminoimidazoles 7 and 10 , [ 26 , 27 ] aminopyrazoles 3 , [ 28 ] 2-amino-3-carboethoxyindoles 12b [ 29 ], and indoline-2-thiones 12a [ 30 ] leads to the formation of [1,2,4]triazolo[4,3- a ]pyrimidinones 8 , imidazo[1,2- a ]pyrimidinones 9 and 11 , pyrazolo[1,5- a ]pyrimidinones 5 , pyrimido[3,2- a ]indolones 14 , and thiopyrano[2,3- b ]indolones 13 .…”

Anticancer Activity Screening of a Series of Imidazo[2,1‐c][1,2,4]triazolone and Imidazo[1,2 ‐b][1,2,4]triazolone Derivatives Synthesized Under Solvent Free Conditions

“…Imidazo[1,2,4]triazoles synthesis was also reported by refluxing 4,5‐dichloro‐1 H ‐imidazol‐1‐yl carbonitrile with hydrazine hydrate and triethylamine . Starting from aminotriazoles, different imidazo[1,2,4]triazole derivatives could be synthesized either through the multicomponent reaction of aminotriazole derivatives with aldehydes and isocyanides or reaction with alkylating agents . Moreover, some fusion or microwave assisted reactions of triazole derivatives were applied as green synthetic pathways of different imidazo[1,2,4]triazoles.…”