Novel heterocyclic outer-ring dienes: N-alkyland N-aryl substituted 4,5-dimethylene-2-oxazolidinones

Raúl Hemández; JoséM M. Sánchez; Adriana Gómez; Gonzalo Trujillo; Rossana Aboytes; Gerardo Zepeda; Roderick W. Bates; Joaquin Tamariz

doi:10.3987/com-93-6407

Novel heterocyclic outer-ring dienes: N-alkyland N-aryl substituted 4,5-dimethylene-2-oxazolidinones

Raúl Hemández^*, JoséM M. Sánchez, Adriana Gómez, Gonzalo Trujillo, Rossana Aboytes, Gerardo Zepeda, Roderick W. Bates, Joaquin Tamariz

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

Abstract

The one-pot synthesis of the hitherto unknown N-substituted 4,5-dimethylene-1,3-oxazolidin-2-ones from diacetyl and the corresponding isocyanate in the presence of triethylamine is described. Diene (4a) undergoes Diels-Alder cycloaddition with N-phenylmaleimide (10), and, in the absence of a dienophile, gives a mixture of dimers (12) and (13), and the ring closure cyclobutene (14).

Original language	English
Pages (from-to)	1951-1956
Number of pages	6
Journal	Heterocycles
Volume	36
Issue number	9
DOIs	https://doi.org/10.3987/com-93-6407
Publication status	Published - Sept 1 1993
Externally published	Yes

ASJC Scopus Subject Areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "Novel heterocyclic outer-ring dienes: N-alkyland N-aryl substituted 4,5-dimethylene-2-oxazolidinones",

abstract = "The one-pot synthesis of the hitherto unknown N-substituted 4,5-dimethylene-1,3-oxazolidin-2-ones from diacetyl and the corresponding isocyanate in the presence of triethylamine is described. Diene (4a) undergoes Diels-Alder cycloaddition with N-phenylmaleimide (10), and, in the absence of a dienophile, gives a mixture of dimers (12) and (13), and the ring closure cyclobutene (14).",

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T1 - Novel heterocyclic outer-ring dienes

T2 - N-alkyland N-aryl substituted 4,5-dimethylene-2-oxazolidinones

AU - Hemández, Raúl

AU - Sánchez, JoséM M.

AU - Gómez, Adriana

AU - Trujillo, Gonzalo

AU - Aboytes, Rossana

AU - Zepeda, Gerardo

AU - Bates, Roderick W.

AU - Tamariz, Joaquin

PY - 1993/9/1

Y1 - 1993/9/1

N2 - The one-pot synthesis of the hitherto unknown N-substituted 4,5-dimethylene-1,3-oxazolidin-2-ones from diacetyl and the corresponding isocyanate in the presence of triethylamine is described. Diene (4a) undergoes Diels-Alder cycloaddition with N-phenylmaleimide (10), and, in the absence of a dienophile, gives a mixture of dimers (12) and (13), and the ring closure cyclobutene (14).

AB - The one-pot synthesis of the hitherto unknown N-substituted 4,5-dimethylene-1,3-oxazolidin-2-ones from diacetyl and the corresponding isocyanate in the presence of triethylamine is described. Diene (4a) undergoes Diels-Alder cycloaddition with N-phenylmaleimide (10), and, in the absence of a dienophile, gives a mixture of dimers (12) and (13), and the ring closure cyclobutene (14).

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M3 - Article

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SN - 0385-5414

VL - 36

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JO - Heterocycles

JF - Heterocycles

IS - 9

ER -

Novel heterocyclic outer-ring dienes: N-alkyland N-aryl substituted 4,5-dimethylene-2-oxazolidinones

Abstract

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