Transformations of 2-[(Methoxy-2-oxoethyl)sulfanyl]-5,6-dihydropyridine under Acid Catalysis: Unexpected Transition to Derivatives of 5,6-Dihydropyridin-2(1H)-one and 2,3,6,7-Tetrahydro-5H-[1,3]thiazolo[3,2-a]pyridine
Derivatives of 2,3,6,7-tetrahydro-5 H -[1,3]thiazolo[3,2- a ]pyridine and 5,6-dihydropyridin-2(1 H )-one were unexpectedly obtained at treating methyl 2-[(6-methyl-3-ethoxy-5,6-dihydropyridin-2-yl)sulfanyl]-acetate with a dilute solution of hydrochloric acid. Their formation resulted from the hydrat...
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Veröffentlicht in: | Russian journal of organic chemistry 2018-05, Vol.54 (5), p.691-695 |
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Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Derivatives of 2,3,6,7-tetrahydro-5
H
-[1,3]thiazolo[3,2-
a
]pyridine and 5,6-dihydropyridin-2(1
H
)-one were unexpectedly obtained at treating methyl 2-[(6-methyl-3-ethoxy-5,6-dihydropyridin-2-yl)sulfanyl]-acetate with a dilute solution of hydrochloric acid. Their formation resulted from the hydration of 5,6-dihydropyridine at the C=N bond accompanied with the elimination of a methyl 2-sulfanylacetate molecule and the addition of the methyl 2-sulfanylacetate to the second 5,6-dihydropyridine molecule at the C
3
=C
4
bond followed by the elimination of a methanol molecule and the closure of a thiazole ring. |
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ISSN: | 1070-4280 1608-3393 |
DOI: | 10.1134/S1070428018050032 |