Journal of Organic Chemistry p. 1206 - 1211 (1986)
Update date:2022-07-30
Topics:
Amin, Shantu
Huie, Keith
Hussain, Nalband
Balanikas, George
Carmella, Steven G.
Hecht, Stephen S.
The syntheses of the 12 isomeric hydroxybenzofluoranthenes (hydroxy-BbF, 1-12) are described. 1-Hydroxy-BbF was prepared by treatment of 1-oxo-1,2,3,3a-tetrahydro-BbF (13) with Pd/C. 2-Hydroxy-BbF was synthesized by reduction of 13 with NaBH4, followed by dehydration, epoxidation, and treatment with Pd/C. 3-Hydroxy-BbF was obtained by reduction of 13 with Zn(Hg) followed by oxidation with Triton-B, dehydration, epoxidation, and aromatization. 4-Hydroxy-BbF and 7-hydroxy-BbF were prepared by reaction of acephenanthrylene with 1-acetoxybutadiene, aromarization, hydrolysis, and separation by HPLC. 5-Hydroxy-BbF was synthesized by reaction of o-bromobenzaldehyde with 3-methoxyfluorene, followed by cyclization with KOH and quinoline, hydrolysis, and purification by HPLC. 6-Hydroxy-BbF was obtained by regiospecific cyclization of 3-methoxy-11H-benzofluorene-11-propionic acid (33), followed by reduction, dehydration, aromatization, and hydrolysis. 8-Hydroxy-BbF was synthesized by dehydration of 7b,8-dihydro-7b,8-dihydroxy-BbF (39). 9-Hydroxy-BbF and 12-hydroxy-BbF were prepared by treatment of the corresponding oxotetrahydro-BbFs with Pd/C. 10-Hydroxy-BbF and 11-hydroxy-BbF were synthesized by reaction of fluorene with the appropriate bromomethoxybenzaldehyde followed by cyclization with hydrolysis.
View MoreContact:+86-571-28186845
Address:Room 1224,Eastcom Mansion,398 Wensan Road,Hangzhou,310013 China
Shaanxi Lighte Optoelectronics Material Co., Ltd.
Contact:+86-29-88320728-622/619/620
Address:No.55 INDUSTRY ROAD 2,XI'AN NATIONAL CIVIL AEROSPACE INDUSTRIAL PARK.XI'AN China 710065.
website:http://www.win-winchemical.com
Contact:0086-577-64498589
Address:6F,No.396 Xingping Road,Longwan Industrial Zone
Jinan Jinguilin Chemical Co.,Ltd
Contact:+86-531-81188412
Address:3rd floor of Torch Building, Huanyuan Rd, City of Jinan
Shandong Xinke Petrochemical Co., Ltd.
Contact:+86-546-7277016
Address:Gudao Industrial Park, Hekou District, Dongying, Shandong Province, China
Doi:10.1016/S0031-9422(00)85513-2
(1986)Doi:10.1021/ja01072a047
(1964)Doi:10.1016/j.tet.2007.09.090
(2008)Doi:10.1021/jo050574s
(2005)Doi:10.1021/jo7021229
(2008)Doi:10.1016/S0040-4039(00)98242-X
(1985)