1-Isoquinolinol was synthesized from isoquinoline via oxidation, reaction with benzoyl chloride and water in yield of 73.3%. According to this process, a method for the synthesis of hydroxyfasudil [1-(1-hydroxy-5-isoquinolinesulfonyl)- homopiperazine] from fasudil [hexahydro-1-(5-isoquinoline-sulfonyl)-1H-1,4-diazepine] was estabilshed in this paper. The process undergoes effectively through protection for amino, oxidation, reaction with water in a water/dichloromethane biphase system in the presence of phase transfer catalyst and benzoyl chloride and then deprotection. The objective product was finally obtained in yield of 46.8% with a purity more than 99% (HPLC). It is virtually a practical process with mild reaction conditions and simple operation.
CHEN Mei-Zhu
,
LIU Shuai
,
WANG Xin-Ran
,
LUO Hao
,
CHEN Li-Gong
,
WANG Dong-Hua
. Synthesis of 1-Isoquinolinol and Hydroxyfasudil[J]. Chinese Journal of Organic Chemistry, 2012
, 32(02)
: 404
-408
.
DOI: 10.6023/cjoc1105252
[1] Satoh, S.; Suzuki, Y.; Harada, T.; Ikegaki, I.; Asano, T.; Shibuya, M.; Sugita, K.; Hidaka, H. Eur. J. Pharmacol. 1992, 220, 243.
[2] Masayuki, I.; Atusuya, T.; Yuji, O.; Takehisa, K.; Yoshimichi, T.; Hiroshi, O.; Motoko, S.; Terumi, S.; Kayoko, F.; Hiroshi, I. Bioorg. Med. Chem. 2007, 15, 350.
[3] Dedmer, S.; Reinoud, G.; Johan, Z.; Andrew, J. H.; Herman, M. Eur. J. Pharmacol. 2008, 585, 398.
[4] Duan, W.-G.; Yuan, S.-T.; Liao, H.; Yan, M.; Zhang, L.-Y. Acta Pharmacol. Sin. 2007, 42, 1013 (in Chinese). (段为钢, 袁胜涛, 廖红, 严明, 张陆勇, 药学学报, 2007, 42, 1013.)
[5] Chen, G.-Y.; Lu, S.-M.; Zhou, Y.-G. Chin. J. Org. Chem. 2006, 26, 1548 (in Chinese). (陈英国, 卢胜梅, 周永贵, 有机化学, 2006, 26, 1548.)
[6] Frisch, K.; Landa, A.; Saaby, S.; Jфrgensen, K. A. Angew. Chem., Int. Ed. 2005, 44, 6058.
[7] Harjit, S.; Sunil, K. A.; Nageshwar, M. Synth. Commun. 1983, 791.
[8] Alan, R. K.; Andrzej, R. L. Energy Fuels 1992, 6, 439.
[9] Hayashida, M.; Honda, H.; Hamana, M. Heterocycles 1990, 31, 1325.
[10] Daniel, B.; Richard, J. D.; Jeremy, D.; Frances, C. A. G.; Steve, L.; Stephen, R. M.; Ray, O.; Verity, S.; Joanne, W. Bioorg. Med. Chem. Lett. 2007, 17, 562.
[11] Zhou, L.-S.; Feng, Y.-Q.; Zhang, W.; Qu, H.-M. Chem. Propellants Polym. Mater. 1999, 28 (in Chinese). (周立山, 冯亚青, 张伟, 曲红梅, 化学推进剂与高分子材料, 1999, 28.)
[12] Hiromu, K.; Masaru, O. WO 9702260, 1997 [Chem. Abstr. 1997, 126, 157526].
[13] Huang, Z.-H. CN 101092413, 2007 [Chem. Abstr. 2008, 148, 151915].
[14] Han, M.-L. M.S. Thesis, Tianjian University, Tianjin, 2009 (in Chinese). (韩美玲, 硕士论文, 天津大学, 天津, 2009.)
