A convenient synthesis of benzofuro[3,2-c]isoquinolines and naphtho[1′,2′:4,5]furo[3,2-c]isoquinolines |
| |
Authors: | Victor E Kalugin Anatoly M Shestopalov |
| |
Institution: | Russian Academy of Sciences, N. D. Zelinsky Institute of Organic Chemistry, 47 Leninsky pr, 119991 Moscow, Russian Federation |
| |
Abstract: | A convenient method for the preparation of benzofuro3,2-c]isoquinoline derivatives is described. The condensation reaction of methyl 2-(chloromethyl)-benzoate with substituted salicylonitriles 7a-c and intramolecular cyclization of the resulting substituted methyl 2-(2-cyanobenzyl)oxy]benzoates 10a-c using potassium tert-butoxide results in the substituted benzofuro3,2-c]isoquinolin-5(6H)-ones 1a-c. The same sequence of reactions starting from 2-(chloromethyl)benzonitrile and compounds 7a-c gave substituted 5-aminobenzofuro3,2-c]isoquinolines 13a-c. In addition, this method is useful for the synthesis of other heterocycles. For example, using 1-cyano-2-naphthol 16, instead of the salicylonitriles 7a-c, gives naphtho1′,2′:4,5]furo3,2-c]isoquinolines. |
| |
Keywords: | |
本文献已被 ScienceDirect 等数据库收录! |
|