Antifolate chemistry: synthesis of 4-[N-[(6RS)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino]benzoic acid via a (propargyl)Co2(CO)6+ complex |
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Authors: | Bavetsias Vassilios Clauss Rainer Henderson Elisa A |
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Institution: | Cancer Research UK Centre for Cancer Therapeutics at The Institute of Cancer Research, Chemistry Department, Cancer Research UK Laboratory, 15 Cotswold Road, Sutton, Surrey, UK SM2 5NG. vassilio@icr.ac.uk |
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Abstract: | A new route to compound 3 (4-N-(6RS)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopentag]quinazolin-6-yl]-N-(prop-2-ynyl)amino]benzoic acid), a crucial intermediate for the synthesis of potent inhibitors of thymidylate synthase (TS), is described. In this sequence the C6-N10 bond was constructed first, by the reductive amination of 5-acetamido-6-bromoindan-1-one 6 with tert-butyl 4-aminobenzoate, then the cyclopentag]quinazolinone ring was formed and the propargyl group was introduced on the N10-position using the (propargyl)Co2(CO)6+ complex as the electrophilic propargyl reagent. |
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