The unusual thermal transformations of the dimethyl 2,2,3,3-tetramethyl-7a-R-1,2,3,7a-tetrahydroimidazo[1,2-b]isoxazole-6,7-dicarboxylate derivatives

The unusual thermal transformations of the dimethyl 2,2,3,3-tetramethyl-7a-R-1,2,3,7a-tetrahydroimidazo[1,2-b]isoxazole-6,7-dicarboxylate derivatives Full article

Journal

Tetrahedron
ISSN: 0040-4020

Output data

Year: 2008, Volume: 64, Number: 30-31, Pages: 7432-7436 Pages count : DOI: 10.1016/j.tet.2008.05.038

Tags

2,3-dihydroisoxazole; azomethine ylide; rearrangement; 1,2-Sigmatropic shift

Authors

Chukanov Nikita V. , Popov Sergey A. , Romanenko Galina V. , Reznikov Vladimir A.

Affiliations

1	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia
2	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Inst Organ Chem, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Sci, Siberian Branch, Int Tomog Ctr, Novosibirsk 630090, Russia

Dimethyl 2,2,3,3 -tetramethyl-7 a- R- 1,2,3,7a-tetra hydroimidazo[1,2-b]-isoxazol e-6,7 -dicarboxylate derivatives were shown to undergo thermal rearrangement along two competing routes giving rise to dimethyl 2-(2-R-4,5-dihydro-1H-3 lambda-5-imidazol-3-ylidene)-3-oxosuccinate derivatives and (or) dimethyl-2-oxo-3-(1 -R-imidazolidin-2-ylidene)succinates. The latter undergoes intramolecular cyclization producing, in case of N-unsubstituted derivatives, methyl 5,6-dioxo-l-R-2,3,5,6-tetrahydro-IH-pyrrolo[1,2-alimidazol-7carboxylates. (c) 2008 Elsevier Ltd. All rights reserved.

Chukanov N.V. , Popov S.A. , Romanenko G.V. , Reznikov V.A.
The unusual thermal transformations of the dimethyl 2,2,3,3-tetramethyl-7a-R-1,2,3,7a-tetrahydroimidazo[1,2-b]isoxazole-6,7-dicarboxylate derivatives
Tetrahedron. 2008. V.64. N30-31. P.7432-7436. DOI: 10.1016/j.tet.2008.05.038 WOS Scopus РИНЦ

Published print:

Jul 1, 2008

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