Study on direct benzoannelations of pyrrole and indole systems by domino reactions with 4,5-dicyanopyridazine

The title pyridazine 1 was found to undergo hetero Diels–Alder [4+2] cycloadditions on the C(2)–C(3) double bond of pyrrole and indole systems; spontaneous loss of nitrogen from the primary adducts, followed by oxidation processes, afforded the corresponding fully aromatic benzoannelated skeletons i...

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Bibliographic Details
Published inTetrahedron Vol. 58; no. 40; pp. 8067 - 8071
Main Authors Giomi, Donatella, Cecchi, Marco
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 30.09.2002
Elsevier
Subjects
4,5-dicyanopyridazine
Chemistry
Chemistry, Organic
cycloadditions
domino processes
Physical Sciences
pyrrole, indole and carbazole derivatives
Science & Technology
pyrrole, indole and carbazole derivatives
cycloadditions
domino processes
4,5-dicyanopyridazine
VINYLINDENES
PHTHALONITRILES
PYRIMIDINE-DERIVATIVES
DIELS-ALDER REACTIONS
CROSS-COUPLING REACTION
ENAMINES
CARBAZOLES
DIMETHYL ACETYLENEDICARBOXYLATE
pyrrole
3-VINYLINDOLES
indole and carbazole derivatives
IODOPYRIMIDINES
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ISSN0040-4020
1464-5416
DOI10.1016/S0040-4020(02)00958-4

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Summary:The title pyridazine 1 was found to undergo hetero Diels–Alder [4+2] cycloadditions on the C(2)–C(3) double bond of pyrrole and indole systems; spontaneous loss of nitrogen from the primary adducts, followed by oxidation processes, afforded the corresponding fully aromatic benzoannelated skeletons in modest and reasonable yields, respectively. Competitive attacks of the same systems at the strongly electrophilic C-4 carbon of 1 , leading to substitution products, were evidenced. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00958-4