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Synthesis of Indeno[ b ]indole and Naphtho[ a ]carbazole Derivatives Involving Diels‐Alder Reaction of Isobenzofurans
Author(s) -
Sankar Elumalai,
Karunakaran Jayachandran,
Dhivyapirabha Loganathan,
Mohanakrishnan Arasambattu K.
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201701851
Subject(s) - carbazole , tetralones , diels–alder reaction , chemistry , indole test , medicinal chemistry , organic chemistry , stereochemistry , catalysis
Diels‐Alder reaction of 1,3‐diarylisobenzofurans with cyclopenten‐1‐one as well as 2‐cyclohexen‐1‐one in the presence of TMSOTf in DCM at 0 °C furnished 4,5‐diarylbenzo[ e ]inden‐1‐ones and 6,7‐diarylbenzo[ f ]α‐tetralones. The benzo[ e ]inden‐1‐ones/benzo[ f ]α‐tetralones upon Fischer indolization led to the formation of indeno[ b ]indoles and dihydronaphtho[ a ]carbazoles, respectively.