82127-15-9Relevant academic research and scientific papers
Synthesis of some fused heterocyclic systems and their nucleoside candidates
El-Sayed, Hassan A.,Said, Said A.,Amr, Abd El-Galil E.
, p. 833 - 845 (2014/02/14)
A series of pyridofuro compounds were synthesized from 4-(4-chlorophenyl)- 1,2-dihydro-2-oxo-6-(thiophen-2-yl)pyridine-3-carbonitrile (1) as starting material. Alkylation of 1 with ethyl bromoacetate gave the corresponding ester 2, which was condensed with hydrazine hydrate to afford the corresponding acid hydrazide derivative 3. Thrope-Ziegler cyclization of 2 with sodium methoxide gave furo[2,3-b]pyridine derivative 4, which was reacted with thiosemicarbazide, allyl isothiocyanate, formamide or hydrazine hydrate to give furopyridine derivatives 5-8, respectively. The latter compound 8 was cyclized with acetylacetone or formic acid to give the corresponding compounds 9 and 10, respectively. Furthermore, sulfurization of 1 with P2S5 gave the corresponding thioxopyridine 11, which was reacted with glycosyl (or galactosyl) bromide, morpholine or piperidine to give the corresponding thioglycoside 12a,b and Mannich base 14a,b derivatives. The deacetylation of 12a,b gave the corresponding deacetylated thioglycosides 13a,b, respectively. All the newly synthesized compounds were characterized by the elemental analyses and spectroscopic evidences (IR, 1H- and 13C NMR).
Studies on the synthesis of some new cyanopyridine-thione and thieno[2,3-b]pyridine derivatives
Mohamed, Omima S.,Al-Taifi, Elham A.,El-Emary, Talaat I.,Bakhite, Etify Abdel-Ghafar
, p. 1061 - 1082 (2008/02/01)
The work included in this article involves the synthesis of new cyanopyridinethiones as good synthons for new thieno[2,3-b]pyridines with anticipated biological activities. Thus, the reaction of -aryl - thiocarbamoylacrylonitrile (1a-c) with (2-thenoyl)-,-trifluoroacetone led to an unexpected formation of 4-aryl-3-cyano-6-(2-thienyl)pyridine-2(1H)-thiones (4a-c). In contrast, the reaction of 1a,b with ethyl acetoacetate produced 4-aryl-3-cyano-5-ethoxycarbonyl-6-methylpyridine-2(1H)-thiones (12a,b). The reaction of compound 4a with methyl iodide gave 2-methylthio derivative 6, which upon treatment with hydrazine hydrate furnished pyrazolopyridine 7. Treatment of 4a-c with chloroacetaimde, in the presence of sodium ethoxide, led to the formation of 3-amino-4-aryl-6-(2-thienyl)thieno[2,3-b]pyridine-2-carboxamides (8a-c). The reactions of 8a with some aromatic aldehydes and/or cycloalkanones were carried out and their products were identified. Compounds 12a,b were reacted with chloro-N-arylacetamides to give ethyl 4-aryl-2-(N-aryl) carbamoylmethylthio-3-cyano-6-methylpyridine-5-carboxylates (13a-j). Upon treatment of compounds 13a-j with sodium alkoxide in alcohol, they underwent an intramolecular Thorpe-Ziegler cyclization to furnish ethyl 3-amino-4-aryl-2-(N- aryl)carbamoyl-6-methylthieno[2,3-b]pyridine-5-carboxylates (14a-j). Compounds 14a-j, in turn, were reacted with triethyl orthoformate and/or carbon disulfide to give corresponding pyridothienopyrimidinone derivatives 15a-j and 18. Pyridothienotriazinone analogs 17a-j were synthesized via diazotisation of compounds 14a-j.
Synthesis and reactions of some new heterocyclic compounds containing the thienylthieno[2,3-b]pyridine moiety
Bakhite, Etify A.,Abdel-Rahman, Abdu E.,Mohamed, Omima S.,Thabet, Eman A.
, p. 1983 - 2006 (2007/10/03)
(4-Aryl-3-cyano-6-(2-thienyl)pyridin-2-ylthio)acethydrazides (5a-c), 3-amino-4-aryl-6-(2-thienyl)thieno[2,3-b]pyridine-2-carbohydrazides (6a-c) and 3-amino-4-phenyl-6-(2-thienyl)thieno[2,3-b]pyridine-2-carboxylic acid (30) were prepared and employed as key intermediates in the synthesis of the title compounds.
Some reactions of 2-functionalized 3-amino-4-aryl-6-(2′-thienyl)-thieno[2,3-B]-pyridines: Synthesis of new pyridothienopyrimidines, pyridothienotriazines and related fused tetracyclic systems
Abdel-Rahman,Bakhite,Mohamed,Thabet
, p. 89 - 106 (2007/10/03)
4-Aryl-3-cyano-6-(2′-thienyl)-pyridine-2(1H)-thiones (2a-c) were prepared and reacted with chloroacetonitrile or chloroacetamide to furnish 3-amino-4-aryl-6-(2′-thienyl)-thieno[2,3-b]pyridine-2-carbonitriles (4a-c) and 2-carboxamide analogs 6a-c respectiv
CYCLIZATION OF NITRILES. XVII. METHODS FOR THE PRODUCTION OF 4,6-DIARYL-3-CYANO-2(1H)-PYRIDINETHIONES AND THEIR MASS-SPECTROMETRIC INVESTIGATION
Promonenkov, V. K.,Shestopalov, A. M.,Sharanin, Yu. A.,Litvinov, V. P.,Rodinovskaya, L. A.,et al.
, p. 1797 - 1802 (2007/10/02)
The boundaries of the methods for the synthesis of 2(1H)-pyridinethiones were extended.The reactions of 3-aroyl-2-aryl- and 3-aroyl-2-aryl-1-bromo-1,1-dicyanopropanes with sodium and morpholinium hydrosulfides and thiourea and of arylidenecyanothioacetamides and 3-aryl-2,4,4-tricyano-3-butenethioamides with acetophenone, and 1-(1-piperidino)-1-phenylethylene, and also the reactions of monothiodibenzoylmethane and 1,3-diphenyl-1-(1-piperidino)-1-propene-3-one with cyanothioacetamide, leading to 4,6-diaryl-3-cyano-2(1H)-pyridinethiones, were investigated.The use of substituted cyanothioacetamides seems most promising.Mass-spectrometric investigation of the obtained thiones showed that the main direction in the dissociation of their molecular ions is the elimination of the H, HS., and CS particles with the formation of the thiazepinium and pyridinium ions and the corresponding radical-cation of pyrrole.
