Synthesis of 2-thioxohydropyridine-3-carbonitrile, 2-alkylthiopyridine, thienopyridine, pyrazolopyridine derivatives and their theoretical calculations

被引：15
作者：
Attaby, FA [1 ]
Elghandour, AHH [1 ]
Mustafa, HM [1 ]
Ibrahem, YM [1 ]
机构：
[1] Cairo Univ, Fac Sci, Dept Chem, Giza, Egypt
来源：
JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 2002年 / 49卷 / 04期
关键词：
thieno[2,3-b]pyridin-2-yl)ethan-1-one; thieno[2,3-b]pyridine-2-carboxylate; thieno[2,3-b]pyridin-2-ylarylketone; 2-methylthiopyridine-3-carbonitrile and; pyrazolo[3,4-b]pyridine-3-ylamine;
D O I：
10.1002/jccs.200200087
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Cyanothioacetamide (1) reacted with but-2-enal (2) to give the corresponding 4-methyl-2-sulfanyl-pyridine-3-carbonitrile (7) which was used as a good starting material for the synthesis of 1-(3-amino-4-methylthieno[2,3-b]pyridin-2-yl)ethan-1-one (10), 3-amino-4-methylthieno[2,3-b]pyridine-2-carboxamide (15), 3-amino-4-methylthieno[2,3-b]pyridine-2-carboxylate (18) and 3-amino-4-methylthieno[2,3-b]pyridin-2-ylarylketone 25a-c through its reactions with each of (1-chloroacetone (8), 3-chloropentane-2,4-dione (11) or ethyl 2-chloro-3-oxo-butanoate (19)), 2-chloroacetamide (13), ethyl 2-chloroacetate (16) and 2-bromo-1-arylethan-1-one 23a-c, respectively. Considering the data of elemental analyses, IR, H-1 NMR, mass spectra and theoretical calculations, structures of the newly synthesized heterocyclic compounds were elucidated.
引用
收藏
页码：561 / 569
页数：9
相关论文
共 24 条
[1]  
ACHET M, 1995, BRIT J HAEMATOL, V91, P434
[2]   Synthesis and antimicrobial evaluation of several new pyridine, thienopyridine and pyridothienopyrazole derivatives [J].
Attaby, FA ;
Elneairy, MAA ;
Elsayed, MS .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1999, 149 :49-64
[3]   Reactions with cyanothioacetamide derivative: Synthesis and reactions of some thieno[2,3-b]pyridine, pyridothienopyridazine, pyrazolo[3,4-b]pyridine and pyridopyrazolo-1,2,4-triazine derivatives [J].
Attaby, FA ;
AbdElFattah, AM .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1996, 119 :257-270
[4]   Reactions with pyridinethione derivatives:: Synthesis and characterization of thienyl[2,3-b]pyridine, pyrido[2′,3′:4,5] thieno[2,3-b]pyridazine, pyrido[2′,3′:4,5] thieno[2,3-b]-pyrimidinone, pyrazolino[3′,4′:4,5] thieno[2,3-b]pyridine and aminopyrazolo[3,4-b]pyridine derivatives [J].
Attaby, FA .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1997, 126 :27-38
[5]   Reactions of styrylthienyl ketone, styryl furyl ketone with thiocyanoacetamide:: Synthesis of several new pyridines, thieno[2,3-b]pyridines, pyrido [2′,3′:4,5]thieno[3,2-c]pyridazines and pyrido-[3′,2′:4,5]thieno[3,2-d]pyrimidin one derivatives [J].
Attaby, FA .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1998, 139 :1-12
[6]   A novel synthesis of 5-hydrazono-4a,7-dihydrodipyrazolo[3,4-b;4,3-e]pyridin-3(2H)-ones and their cyclization to fused triazines [J].
Attaby, FA ;
Eldin, SM ;
El-Neairy, MAA .
JOURNAL OF CHEMICAL RESEARCH, 1998, (10) :632-633
[7]  
Attaby FA, 1998, HETEROATOM CHEM, V9, P571, DOI 10.1002/(SICI)1098-1071(1998)9:6<571::AID-HC8>3.0.CO
[8]  
2-7
[9]   A novel synthesis of thienopyridine, pyrroloquinolinothiophene, pyrazolopyridin-3-yl-phenylthiourea and thiazolylpyrazolopyridine derivatives [J].
Attaby, FA ;
Abd El-Fattah, AM .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1999, 155 :253-270
[10]  
ATTABY FA, 1998, J CHEM RES M, V10, P2754
123