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DOI: 10.1055/s-2002-20952
Synthesis of Angular Pyrrolocoumarins
Publikationsverlauf
Publikationsdatum:
28. Juli 2004 (online)
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Abstract
The new pyrrolocoumarin 3 was synthesized in two steps from 7-amino-4-methylcoumarin by selective o-chloroacetylation at position 8 and subsequent cyclization (the Sugasawa route to indoles). Regioselective inverse electron demand Diels-Alder reaction of 3 with dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate or 3,6-bis(trifluoromethyl)-1,2,4,5-tetrazine then gave the angular pyridazinepyrrolocoumarins 4 and 5, respectively, in good yield.
Key words
antitumour agents - Diels-Alder reaction - electrophilic aromatic substitution - indoles - polycycles
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References
Atomic positions, a full list of bond lengths and angles and other crystallographic data have been deposited as Supplementary Publication No. CCDC 175053. Copies can be obtained from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk).