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Synthesis 2002(4): 0475-0478
DOI: 10.1055/s-2002-20952
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Angular Pyrrolocoumarins

José Carlos Gonzáleza, Joana Lobo-Antunesa, Paulo Pérez-Louridob, Lourdes Santanaa, Eugenio Uriarte*a
a Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Fax: +34(981)594912; e-Mail: qofuri@usc.es;
b Departamento de Química Inorgánica, Facultade de Ciencias, Universidade de Vigo, 36200 Vigo, Pontevedra, Spain
Further Information

Publication History

Received 3 December 2001
Publication Date:
28 July 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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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).