Bibliographic Details
| Title: |
Multicomponent Cyclization of Ethyl Trifluoroacetoacetate with Acetaldehyde and 1,3-Diamines to Hetero-Fused Pyridines. |
| Authors: |
Kushch, S. O.1 (AUTHOR), Goryaeva, M. V.1 (AUTHOR) pmv@ios.uran.ru, Surnina, E. A.1 (AUTHOR), Burgart, Ya. V.1 (AUTHOR), Saloutin, V. I.1 (AUTHOR) |
| Source: |
Russian Journal of Organic Chemistry. Dec2023, Vol. 59 Issue 12, p2147-2156. 10p. |
| Subject Terms: |
*RING formation (Chemistry), *CHEMICAL synthesis, *DIAMINES, *NUCLEAR magnetic resonance spectroscopy, *ACETALDEHYDE, *X-ray spectroscopy, *PYRIDINE derivatives |
| Abstract: |
A procedure has been developed for the synthesis of cis- and trans-diastereoisomeric partially hydrogenated pyrido[1,2-a]pyrimidines and pyrido[2,1-b]quinazolines by the four-component cyclization of ethyl trifluoroacetoacetate with two acetaldehyde molecules and propane-1,3-diamine or 2-(aminomethyl)-aniline. The reactions are accompanied by side formation of zwitterionic tetrahydropyrimidinium carboxylate in the reaction with propane-1,3-diamine and of 7-hydroxy-7-(trifluoromethyl)-5,5a,6,7,8,11-hexahydro-9H-pyrido[2,1-b]quinazolin-9-one in the reaction with 2-(aminomethyl)aniline; in the latter case, the cyclization involved one acetaldehyde molecule. The stereochemical structure of the synthesized compounds was determined by 1H, 19F, and 13C NMR spectroscopy and X-ray analysis. A probable mechanism has been proposed for the formation of new hetero-fused pyridine derivatives. [ABSTRACT FROM AUTHOR] |
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