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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 192, 2017 - Issue 1
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Original Articles

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

Victor V. DotsenkoDepartment of Chemistry and High Technologies, Kuban State University, Krasnodar, Russian Federation;Department of Chemistry, North Caucasus Federal University, Stavropol, Russian FederationCorrespondence[email protected]
,
Ivan S. BushmarinovLaboratory for X-Ray Diffraction Studies, A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
,
Alexander S. GoloveshkinLaboratory for X-Ray Diffraction Studies, A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
,
Elena A. ChigorinaLaboratory of Custom Organic Synthesis, State Enterprise IREA, Moscow, Russian Federation
,
Konstantin A. FrolovDepartment of Chemistry and High Technologies, Kuban State University, Krasnodar, Russian Federation
&
Sergey G. KrivokolyskoDepartment of Chemistry and High Technologies, Kuban State University, Krasnodar, Russian Federation
Page 0 | Received 01 May 2016, Accepted 11 Aug 2016, Published online: 21 Oct 2016
 
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ABSTRACT

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.

GRAPHICAL ABSTRACT

Funding

V.V.D. is grateful for financial support by the Russian Ministry of Education and Science (State Assignment to Higher Education Institutions, project No. 547).

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