Synthesis and antimicrobial activity of new functionalized derivatives of [1,2,4]triazolo[4,3‐a]pyrimidin‐5(1H)‐one

Abstract

New functionalized 1,7‐diaryl‐6‐cyano‐1,2,4‐triazolo[4,3‐a]pyrimidin‐5(1H)‐one derivatives (5a–j) were synthesized via reaction of 5‐cyano‐6‐phenyl‐2‐thiouracil 1 with the respective hydrazonoyl halides 2a–j and their biological activity was evaluated. The mechanism and the regioselectivity of the studied reactions are discussed. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:393–398, 2007; Published online in Wiley InterScience (http://www.interscience.wiley.com). DOI 10.1002/hc.20311

Design, Synthesis, Antiviral Evaluation, and Molecular Dynamics Simulation Studies of New Spirocyclic Thiopyrimidinones as Anti HCoV‐229E

“…Compound 9 is a valuable starting substrate for different reactions like the formation of some azodyes (Scheme 4) as it has two different active methine centers either at the terminal site, or at C-5 of thiouracil cycle. According to literature reports, similar thiouracils with just terminal active methine center undergo diazocoupling at this site giving either the isolable azo products [23][24][25] or triazolopyrimidine derivatives via instant cyclization of the formed azo compounds under the reaction conditions. [26,27] For our molecules, it was expected that there would be a competition between the two centers to undergo the dizaocoupling, to form three possible azo derivatives 11, 12, and 13 as shown in (Scheme 5).…”

Synthesis and Biological Activity of Novel Thieno [2,3-d] [1,2,4] triazolo [4,3-a] pyrimidine and Pyrazolo [3,4-c] pyrazole Derivatives

“…The biological (1)(2)(3) , bactericidal (4) and medicinal (5,6) activities of theino [2,3-d] pyrimidine derivatives have recently attracted considerable attention (7,8) . In view of the above findings and in continuation to our interest on the use of hydrazonoyl halides for the synthesis of heterocyclic compounds incorporating different functionalities of biological importance (9,10) we reported here a facile and short synthesis of the title compounds starting from either 2,4-thioxo-1,2,3,4,5,6,7-hexahydro-4H-cyclopenta [4,5] thieno [2,3-d] pyrimidin-2,4-dithione (1) or 2(4-dihydro-5-oxo-3-methyl-1H-pyrazolo-1-yl)-5,6,7,8-tetrahydrothieno [2,3-d] pyrimidin-4 (3H,1H)-one (11) and hydrazonoyl halides (2) .…”

Chemical and Photochemical Studies on 1,8-Diaminonaphthalene

“…On the other hand, compounds 1,4-, 1,5diazepine derivatives and their analogs have emerged as a successful class of CNS drugs that are used as hypnotics (sleep inducers), anti-anxiety agents, anticonvulsants, muscle relaxants and are being evaluated as therapeutic agents for the treatment of AIDS [11][12][13]. These common features along with our previous work of using hydrazonoyl halides in the synthesis of interesting fused heterocyclic compounds incorporating different functionalities of biological importance [14][15][16][17] have motivated us to seek for straightforward routes for the synthesis of new derivatives of naphthodiazepine, thiazinoperimidine, triazolo-perimidine, and thiazoloperimidine. Moreover, the irradiation of 1,8diaminonaphthalene 1 was studied using a highpressure mercury lamp in the presence of oxygen.…”