Multicomponent Cyclizations of Ethyl Trifluoroacetoacetate with Acetaldehyde and 1,3-Diamines to Heteroannulated Pyridines

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Abstract

A four-component approach was developed for the synthesis of cis- and trans-diastereomeric partially hydrogenated pyrido[1,2-a]pyrimidines and pyrido[2,1-b]quinazolines based on the cyclization of ethyl trifluoroacetoacetate with two acetaldehyde molecules and 1,3-diaminopropane or 2-aminomethylaniline. The zwitterionic salt of tetrahydropyrimidine was isolated as a by-product from the reaction with 1,3-diaminopropane. And from the reaction with 2-aminomethylaniline 7-hydroxy-7-(trifluoromethyl)-5,5a,6,7,8,11-hexahydro-9H-pyrido[2,1-b]quinazolin-9-one was obtained as a result of the participation of one aldehyde molecule. The diastereomeric structure of the synthesized heterocycles was established on the basis of 1Н, 19F, 13С NMR spectroscopy and XRD. A mechanism for the formation of new heteroannulated pyridines was proposed.

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About the authors

S. O. Kushch

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Author for correspondence.
Email: pmv@ios.uran.ru
ORCID iD: 0000-0002-7518-8998
Russian Federation, Ekaterinburg

M. V. Goryaeva

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: marinavgoryaeva@gmail.com
ORCID iD: 0000-0002-7853-688X
Russian Federation, Ekaterinburg

E. A. Surnina

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: pmv@ios.uran.ru
ORCID iD: 0000-0003-2961-6450
Russian Federation, Ekaterinburg

Ya. V. Burgart

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: pmv@ios.uran.ru
ORCID iD: 0000-0001-6061-2410
Russian Federation, Ekaterinburg

V. I. Saloutin

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: pmv@ios.uran.ru
ORCID iD: 0000-0003-1976-7861
Russian Federation, Ekaterinburg

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Supplementary files

Supplementary Files
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1. JATS XML
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2. Fig. 1. SSCC of diastereotopic protons in heterocycles 4, 6, 7

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3. Fig. 2. General view of the molecule of compound 4trans according to X-ray diffraction data with atoms represented by thermal vibration ellipsoids with 30% probability

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4. Fig. 3. General view of the molecule of compound 4cis according to X-ray diffraction data with atoms represented by thermal vibration ellipsoids with 30% probability

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5. Fig. 4. General view of the molecule of compound 5 according to X-ray diffraction data with atoms represented by thermal vibration ellipsoids with a 30% probability

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6. Scheme 1

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7. Scheme 2

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8. Scheme 3

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