[4+2]-CYCLOADDITIONS OF 3-AMINO-4-IMINO-4H-THIENO[3,4-C][1]BENZOPYRAN WITH SOME SELECTED DIENOPHILES

3-Amino-4-imino-4H-thieno[3,4-c][1] benzopyran 1 adds dimethyl maleate 2 and dimethyl acetylenedicarboxylate 6 in a [4 + 2] mode across the thiophene ring and reacts with 2,3-dichloro-1,4-naphthoquinone 12 by substitution of both chlorine atoms. All primary adducts. 3, 7 and 13. however, are unstabl...

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Published inJ. Chem. Soc., Perkin Trans. 1 no. 15; pp. 2191 - 2195
Main Authors NYIONDIBONGUEN, E, FONDJO, ES, FOMUM, ZT, DOPP, D
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 1994
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
Oxygen sulfur heterocycle
Dimethyl butynedioate
Polycyclic compound
Cycloaddition
Aromatic compound
Tricyclic compound
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Summary:3-Amino-4-imino-4H-thieno[3,4-c][1] benzopyran 1 adds dimethyl maleate 2 and dimethyl acetylenedicarboxylate 6 in a [4 + 2] mode across the thiophene ring and reacts with 2,3-dichloro-1,4-naphthoquinone 12 by substitution of both chlorine atoms. All primary adducts. 3, 7 and 13. however, are unstable under the reaction conditions. The structures of the final products 4, 10 and 15 have been assigned from their spectral data and their formation has been rationalized in terms of transformations available to the assumed primary products.
ISSN:0300-922X
2050-8255
1364-5463
DOI:10.1039/p19940002191