Synthesis of thiazolo[3,2-a]pyridines via an unusual Mannich-type cyclization

被引：13

作者：

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

Bushmarinov, Ivan S. ^{[3
]}

Goloveshkin, Alexander S. ^{[3
]}

Chigorina, Elena A. ^{[4
]}

Frolov, Konstantin A. ^{[1
]}

Krivokolysko, Sergey G. ^{[1
]}

机构：

[1] Kuban State Univ, Dept Chem & High Technol, Krasnodar 350040, Russia

[2] North Caucasus Fed Univ, Dept Chem, Stavropol, Russia

[3] Russian Acad Sci, Lab Xray Diffract Studies, AN Nesmeyanov Inst Organoelement Cpds, Moscow, Russia

[4] State Enterprise IREA, Lab Custom Organ Synth, Moscow, Russia

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2017年 / 192卷 / 01期

关键词：

Thiazolo[3; 2-a]pyridines; aminomethylation; Mannich reaction; X-ray studies; bis(pyrid-2-yl)disulfides; ONE-POT SYNTHESIS; N; S-CONTAINING HETEROCYCLES; AMINOMETHYLATION; CYANOTHIOACETAMIDE; DERIVATIVES; CHEMISTRY;

D O I：

10.1080/10426507.2016.1224877

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The Mannich-type reaction of N-methylmorpholinium 4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates with 3-(1,3-benzodioxol-5-yl)-2-methylpropanal (ocean propanal) and p-toluidine afforded 7-aryl-2-(1,3-benzodioxol-5-ylmethyl)-2-methyl-3-[(4-methylphenyl)amino]-5-oxo-2,3,6,7-tetrahydro-5H-thiazolo[3,2-a]pyridine-8-carbonitriles in modest (25-46%) yields. The structure of the key compound was confirmed by X-ray crystal structure analysis.

引用

页码：47 / 52

页数：6

共 50 条

[1] Approaches to the synthesis of thiazolo[3,2-a]pyridines (microreview)
Chaban, Taras I.
Lelyukh, Maryan I.
Chaban, Ihor H.
Kasyanchuk, Olga Y.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2024, 60 (3-4) : 124 - 126
[2] Synthesis of thiazolo[3,2-a]pyridines from enaminoesters by tandem conjugate addition-cyclization
Caballero, E
Puebla, P
Medarde, M
Honores, Z
Sastre, P
López, JL
San Feliciano, A
TETRAHEDRON LETTERS, 1998, 39 (5-6) : 455 - 458
[3] ANTITRICHOMONAL ACTIVITY OF MESOIONIC THIAZOLO[3,2-A]PYRIDINES
WALKER, KAM
SJOGREN, EB
MATTHEWS, TR
JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (11) : 1673 - 1679
[4] Synthesis of some new thiazolo[3,2-a]pyridines and related heterocyclic systems
Al-Thebeiti, MS
FARMACO, 2000, 55 (02): : 109 - 118
[5] A new route to partially hydrogenated thiazolo[3,2-a]pyridines
Dyachenko, AD
Desenko, SM
Dyachenko, VD
Chernega, AN
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2004, (05): : 765 - 775
[6] SYNTHESIS OF SUBSTITUTED THIAZOLO[3,2-A]QUINAZOLINES
GAKHAR, HK
KIRAN, S
GUPTA, SB
JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1982, 59 (05) : 666 - 667
[7] SYNTHESIS OF SOME THIAZOLO[3,2-A]PYRIMIDINES
GEIES, AA
KAMALELDEAN, AM
ELHAFEZ, AAA
GABER, AM
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1991, 56 (1-4): : 87 - 93
[8] SYNTHESIS OF THE THIAZOLO[3,2-a]QUINOLINIUM SYSTEM
Kim, D. G.
Vershinina, E. A.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2010, 46 (06) : 773 - 774
[9] An efficient synthesis of thiazolo[3,2-a]pyrimidinones
Ahmad, Nadia M.
Jones, Keith
TETRAHEDRON LETTERS, 2010, 51 (25) : 3263 - 3265
[10] Synthesis of the thiazolo[3,2-a]quinolinium system
D. G. Kim
E. A. Vershinina
Chemistry of Heterocyclic Compounds, 2010, 46 : 773 - 774

← 1 2 3 4 5 →