160450-75-9Relevant academic research and scientific papers
Design and synthesis of pyrido[2,1- b ][1,3,5]thiadiazine library via uncatalyzed mannich-type reaction
Dotsenko, Victor V.,Frolov, Konstantin A.,Pekhtereva, Tatyana M.,Papaianina, Olena S.,Suykov, Sergey Yu.,Krivokolysko, Sergey G.
, p. 543 - 550 (2014/12/10)
This Research Article describes the synthesis of an over 700-member library of (8R/8S)-3-R-8-aryl-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazin-9-carbonitriles by uncatalyzed Mannich-type reaction of N-methylmorpholinium (4R/4S)-4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridin-2-thiolates with a set of primary amines and excessive HCHO. The scope and limitations of the reaction were studied. Starting thiolates were obtained in yields of 53-82% by multicomponent reaction of aromatic aldehydes, cyanothioacetamide, 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid), and N-methylmorpholine, followed by heterocyclization of the resulting Michael adducts.
A novel synthesis of pyridine-2(1H)-thione, pyrazolo[3,4-b]pyridine, pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidine, thieno[2,3-b]pyrdine, and pyrido[3',2':4,5]thieno[3,2-d]pyrimidine derivatives containing a naphthyl moiety
Fattah, Azza M. Abdel,Elneairy, Mohamed A. A.,Gad-Elkareem, Mohamed A. M.
, p. 1351 - 1364 (2008/02/11)
6-Amino-4-naphthyl-2-thioxo-1,2-dihydropyridine-3,5-dicarbonitriles 3a, b were synthesized from the reaction of naphthaldehydes 1a, b and cyanothioacetamide (2). Compounds 3a, b were taken as starting materials for the synthesis of pyrazolo[3,4-b]pyridine 7a, b, and 8a, Pyrido-[2',3':3,4] pyrazolo[1,5-a]pyrimidine 9a, b; thieno[2,3-b]pyridine 16a-d, 18a, b, 21a-d, 24a, b, and 25a; and pyrido[3,2:4,5]thieno[3,2-d]pyrimidine 17a, b derivatives through their reactions with the corresponding reagents. All structures of the newly synthesized heterocyclic compounds were established on the basis of IR, 1H NMR, 13C NMR, mass spectra, and elemental analyses.
Cyanothioacetamide in heterocyclic chemistry: Synthesis of thiopyran, pyridinethione, thienopyridine, pyridothienotriazine and pyridothienopyrimidine derivatives
Elneairy, Mohamed A.A.,Eldin, Sanaa M.,Attaby, Fawzy A.,El-Louh, Ali K.K.
, p. 289 - 302 (2007/10/03)
Cyanothioacetamide (1) reacted with α- and β-naphthaldehyde 2a,b to afford the corresponding 3-naphthyl-2-thiocarboxamidopropenonitriles 3a,b. Compounds 3a,b structures could be elucidated via their reactions with acrylonitrile, ethyl acrylate (4a,b), N-arylmaleimides 6a-c and ethyl acetoacetate (8). The isolated products could be represented as the thiopyran, thiopyranopyrrolidine and pyridinethione derivatives 5a-d, 7a-f and 9a,b respectively. Pyridinethiones 9a,b had been used as the starting materials in the present study in addition to the next ones to synthesize several new thienopyridines, pyridothienotriazine and pyridothienopyrimidines 12a-f, 15a,b, 16b, 17-19a,b respectively through their reactions with the corresponding reagents. All structures of the newly synthesized heterocyclic compounds were established on the basis of the data of IR, 1H NMR and elemental analyses.
