Synthesis of Polynuclear Heterocyclic Compounds Derived from Thieno[2,3-d]pyrimidine Derivatives

Abstract

Abstract:Reaction of 2-hydrazino-3-methyl-3,4-dihydrothieno [2,3-d]pyrimidin-4-one derivatives 2a,b with aliphatic acids afforded the thienotriazolopyrimidinone derivatives 3a-d, with nitrous acid yielded tetrazolothienopyrimidinone derivatives 4a,b and with carbon disulphide furnished 3-mercaptothienotriazolopyrimidinone derivatives 5a,b. Also, 2a,b reacted with aldehydes to afford the arylhydrazones 6a-f which cyclized into thienotriazolopyrimidinone derivatives 7a-f. Furthermore, 2a,b condensed with ethyl acetoacetate and ethyl cyanoacetate to afford 2-(1-pyrazolyl) derivatives 9a,b and 10a,b, respectively. On the other hand, 2-hydrazino derivatives 2a,b condensed with α-halo-ketones to yield thienpyrimidotriazinone derivatives 11a,b and with β-diketones, to form 2-(1-pyrazolyl) derivatives 12a-f.

Synthesis and Kinetic Testing of Tetrahydropyrimidine‐2‐thione and Pyrrole Derivatives as Inhibitors of the Metallo‐β‐lactamase from Klebsiella pneumonia and Pseudomonas aeruginosa

“…The pyrrole derivatives 10a–10c were converted to the corresponding pyrrolo[2,3‐ d ]pyrimidine‐2‐thiones 11a–c by heating (38) with thiourea in ethanol. Ethylation (39–41) of 11a–c with ethyl iodide in the presence of base gave the corresponding S‐ethyl pyrimidine derivatives 12a–12c (Figure 6).…”

“…The pyrrole derivatives 10a-10c were converted to the corresponding pyrrolo[2,3-d]pyrimidine-2-thiones 11a-c by heating (38) with thiourea in ethanol. Ethylation (39)(40)(41) of 11a-c with ethyl iodide in the presence of base gave the corresponding S-ethyl pyrimidine derivatives 12a-12c ( Figure 6). Heating (43,44) 7a-c with chloroacetyl chloride in refluxing dioxane afforded the pyrrolopyrimidine-4-one derivatives 17a-c, which on reaction with hydrazine hydrate in refluxing ethanol gave the hydrazinomethyl derivatives 18a-c.…”

Synthesis of Some Thienopyrimidine Derivatives

“…The structures of compounds 1-10 were confirmed from their IR, 1 H-NMR, 13 C-NMR and MS spectral data. Substitution of the mercapto group in 4a,d by hydrazine hydrate afforded the 2-hydrazino derivative 11 which was then cyclized by glacial acetic acid to give the triazolo derivative 12 [17,18]; the latter compound is sparingly soluble in CDCl 3 and DMSO-d 6 , precluding the use of 13 C-NMR spectroscopy as a characterization tool. Oxidation of 4a,d by iodine (Scheme 3) gave the disulfides 13a,b [19].…”

Synthesis, antimicrobial, antioxidant activities of novel 6-aryl-5-cyano thiouracil derivatives

“…These hydrazino derivatives exerted promising antibacterial, antifungal and anticancer activities [17][18][19]. In addition, the reactions of hydrazino pyrimidines with formic acid, trietylorthoformate(TEOF)and CS 2 (one carbon donor moieties) afforded the corresponding triazolopyrimidines [20][21][22][23][24][25],which are known to exhibit interesting Pharmaceutical activities [26,27]. In the light of the aforementioned facts, and in continuation for our interest in the synthesis of biologically active heterocyclic compounds, we report herein the synthesis and biological evaluation of novel 6-aryl-5-cyano thiouracil derivatives as antimicrobial and antioxidant agents.…”