Chemical synthetic method of four main metabolites of quinocetone

2013 
The invention relates to a synthetic method of four main metabolites of 2-Propen-1-one-1-(3-methyl-2-quinoxalinyl)-3-phenyl-, 2-Quinoxaline methanol-3-methyl-Alpha-(2-phenylethenyl)-, 2-Propen-1-one-1-(3-methyl-4-oxide-2-quinoxalinyl)-3-phenyl- and 2-Quinoxaline methanol,3-methyl-Alpha-(2-phenylethenyl)-,1-oxide of quinocetone. The 2-Propen-1-one-1-(3-methyl-2-quinoxalinyl)-3-phenyl- is synthesized in such a manner that mequindox is deoxidized through sodium dithionite to generate the intermediate of 3-methyl-2-acetyl-quinoxaline, and a condensation reaction is conducted between the 3-methyl-2-acetyl-quinoxaline and benzaldehyde so as to obtain the 2-Propen-1-one-1-(3-methyl-2-quinoxalinyl)-3-phenyl-. Then, the carbonyl on the side chain of 2-Propen-1-one-1-(3-methyl-2-quinoxalinyl)-3-phenyl-is reduced through sodium borohydride so as to obtain the 2-Quinoxaline methanol-3-methyl-Alpha-(2-phenylethenyl)-. Mequindox is selectively deoxidized through trimethyl phosphate to generate 2-Propen-1-one-1-(3-methyl-4-oxide-2-quinoxaline), and a condensation reaction is conducted between the 2-Propen-1-one-1-(3-methyl-4-oxide-2-quinoxaline) and benzaldehyde so as to obtain the 2-Propen-1-one-1-(3-methyl-4-oxide-2-quinoxalinyl)-3-phenyl-. Mequindox is selectively deoxidized through appropriate amine to generate 2-Propen-1-one-1-(3-methyl-4-oxide-2-quinoxaline), a condensation reaction is conducted between the 2-Propen-1-one-1-(3-methyl-4-oxide-2-quinoxaline) and benzaldehyde so as to obtain the 2-Propen-1-one-1-(3-methyl-4-oxide-2-quinoxalinyl)-3-phenyl-, and carbonyl on the side chain of 2-Propen-1-one-1-(3-methyl-4-oxide-2-quinoxalinyl)-3-phenyl- is reduced through sodium borohydride so as to obtain the 2-Quinoxaline methanol,3-methyl-Alpha-(2-phenylethenyl)-,1-oxide of quinocetone.
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