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Regioselective Annulation of Unsymmetrical 1,2‐Phenylenebis(diaryl/diheteroarylmethanol): A Facile Synthesis of Anthracene, Tetracene, and Naphtho[ b ]thiophene Analogues
Author(s) -
Sivasakthikumaran Ramakrishnan,
Rafiq Settu Muhammad,
Sankar Elumalai,
Clement J. Arul,
Mohanakrishnan Arasambattu K.
Publication year - 2015
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.201501087
Subject(s) - regioselectivity , tetracene , chemistry , annulation , anthracene , thiophene , naphthalene , acetic acid , benzene , catalysis , organic chemistry , medicinal chemistry , combinatorial chemistry
A systematic study on the regioselective cyclization of benzene‐ and naphthalene‐based unsymmetrical diols with HBr (33 %) in acetic acid at room temperature led to the formation of annulation products. By using this method, synthesis of a wide variety of anthracene, tetracene and naphtho[ b ]thiophene analogues was achieved in good to excellent yields. By employing HBr (33 %) in acetic acid as a catalyst for regioselective cyclization of unsymmetrical diols was very facile and devoid of commonly encountered dihydroisobenzofuran formation.