A New Approach to the Synthesis of Functional Derivatives of 3-(4-Pyridinyl)-1H-indole and 4-(1H-Indol-3-yl)thieno[2,3-b]pyridine

被引：17

作者：

Dotsenko, V. V. ^{[1
,2
]}

Krivokolysko, S. G. ^{[1
]}

Krivokolysko, B. S. ^{[1
]}

Frolov, K. A. ^{[1
]}

机构：

[1] Kuban State Univ, Ul Stavropolskaya 149, Krasnodar 350040, Russia

[2] North Caucasus Fed Univ, Stavropol, Russia

来源：

RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2018年 / 88卷 / 04期

关键词：

cyanothioacetamide; 3-(pyridine-4-yl)-1H-indoles; 6-amino-3,5-dicyanopyridine-2-thiolate; Thorpe-Ziegler cyclization; thieno[2,3-b]pyridines; ADENOSINE A(1) RECEPTOR; PYRIDINE-DERIVATIVES; THIENOPYRIDINES; QUINOLINES; INHIBITORS; CHEMISTRY; AGONISTS; PROFILE; SERIES;

D O I：

10.1134/S1070363218040114

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Sequential reaction of indole-3-carbaldehyde with cyanothioacetamide and KOH led to the formation of potassium 6-amino-4-(1H-indol-3-yl)-3,5-dicyanopyridine-2-thiolate. S-Alkylation of the latter afforded new functional derivatives of 3-(pyridine-4-yl)-1H-indole and 4-(1H-indol-3-yl)-thieno[2,3-b]pyridine.

引用

页码：682 / 688

页数：7

共 37 条

[1] Recent trends in the chemistry of thienopyridines [J].

Bakhite, EAG .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2003, 178 (05) :929-992

[2] New, non-adenosine, high-potency agonists for the human adenosine A2B receptor with an improved selectivity profile compared to the reference agonist n-ethylcarboxamidoadenosine [J].

Beukers, MW ;

Chang, LCW ;

Künzel, JKVD ;

Mulder-Krieger, T ;

Spanjersberg, RF ;

Brussee, J ;

Ijzerman, AP .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (15) :3707-3709

[3] Inhibitors of the RET tyrosine kinase based on a 2-(alkylsulfanyl)-4-(3-thienyl) nicotinonitrile scaffold [J].

Brandt, Wiebke ;

Mologni, Luca ;

Preu, Lutz ;

Lemcke, Thomas ;

Gambacorti-Passerini, Carlo ;

Kunick, Conrad .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (07) :2919-2927

[4] A series of ligands displaying a remarkable agonistic-antagonistic profile at the adenosine A1 receptor [J].

Chang, LCW ;

Künzel, JKVF ;

Mulder-Krieger, T ;

Spanjersberg, RF ;

Roerink, SF ;

van den Hout, G ;

Beukers, MW ;

Brussee, J ;

IJzerman, AP .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (06) :2045-2053

[5] Unexpected result in the reaction of 3-amino-3-thioxopropanamides with 2-anilinomethylene derivatives of 1,3-dicarbonyl compounds. synthesis of pyrimidine-5-carboxamide derivatives [J].

Dotsenko, V. V. ;

Frolov, K. A. ;

Krivokolysko, S. G. ;

Polovinko, V. V. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2013, 49 (03) :440-451

[6] On the regioselectivity of the reaction of cyanothioacetamide with 2-acetylcyclo-hexanone, 2-acetylcyclopentanone, and 2-acetyl-1-(morpholin-4-yl)-1-cycloalkenes [J].

Dotsenko, V. V. ;

Krivokolysko, S. G. ;

Polovinko, V. V. ;

Litvinov, V. P. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (02) :309-319

[7] Unusual reaction of thiomalonamide with 5,5-dimethyl-2-phenylaminomethylidene-1,3-cyclohexanedione [J].

Dotsenko, V. V. ;

Krivokolysko, S. G. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2013, 48 (10) :1568-1570

[8] The synthesis of cyclopenta[c]pyridine (2-pyrindene) derivatives [J].

Dotsenko, Victor V. ;

Krivokolysko, Sergey G. ;

Litvinov, Victor P. .

MONATSHEFTE FUR CHEMIE, 2008, 139 (03) :271-275

[9] The Mannich-Type Synthesis of Macroheterocycles with Pyrido[2,1-b][1,3,5]thiadiazine Unit [J].

Dotsenko, Victor V. ;

Chigorina, Elena A. ;

Papaianina, Elena S. ;

Frolov, Konstantin A. ;

Krivokolysko, Sergey G. .

MACROHETEROCYCLES, 2015, 8 (03) :310-313

[10] Anilinomethylidene derivatives of cyclic 1,3-dicarbonyl compounds in the synthesis of new sulfur-containing pyridines and quinolines [J].

Dotsenko, VV ;

Krivokolysko, SG ;

Chernega, AN ;

Litvinov, VP .

RUSSIAN CHEMICAL BULLETIN, 2002, 51 (08) :1556-1561

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