Regioselective Annulation of Unsymmetrical 1, 2‐Phenylenebis(diaryl/diheteroarylmethanol): A Facile Synthesis of Anthracene, Tetracene, and Naphtho[b]thiophene Analogues. Issue 35 (6th November 2015)

• Record Type: Journal Article
• Authors: Sivasakthikumaran, Ramakrishnan; Rafiq, Settu Muhammad; Sankar, Elumalai; Clement, J. Arul; Mohanakrishnan, Arasambattu K.
• Is Part Of: European journal of organic chemistry. Issue 35(2015)
• Page Start: 7816
• Page End: 7835
• Publication Date: 2015-11-06
• Subjects: Synthetic methods -- Polycycles -- Annulation -- Aromaticity; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201501087
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : Regioselective cyclization of benzene‐ and naphthalene‐based unsymmetrical diols with HBr (33 %) in acetic acid at room temperature led to the formation of annulated arenes and heteroarenes in good to excellent yields.