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Synthesis of Benzo[ k ]fluoranthene Derivatives through Diels–Alder Reaction of 1,3‐Diarylbenzo[ c ]furans
Author(s) -
Karunakaran Jayachandran,
Mohanakrishnan Arasambattu K.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701137
Subject(s) - fluoranthene , chemistry , acenaphthylene , diels–alder reaction , aryne , epoxide , regioselectivity , organic chemistry , medicinal chemistry , dibenzothiophene , dehydration , catalysis , pyrene , biochemistry
Diels–Alder reaction of symmetrical/unsymmetrical benzo[ c ]furans with acenaphthylene in xylenes at reflux temperatures followed by p ‐toluenesulfonic acid‐mediated epoxide cleavage and dehydration furnished diaryl/heteroaryl‐substituted benzo[ k ]fluoranthenes. This strategy could be successfully applied to the synthesis of dimeric and trimeric benzo[ k ]fluoranthenes. Functionalization of representative benzo[ k ]fluoranthene derivatives was also performed. UV/Visible, emission and electrochemical properties of representative fluoranthene derivatives are also reported.