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Letters in Organic Chemistry


ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Synthesis of New 4-(3,4,5-Trimethoxyphenyl)-3H-Furo[3,4-b]Carbazole-3-Ones Derivatives

Author(s): Aurelie Chilloux, Berenger Biannic, Fabien Girault, Maud Antoine, Sylvain Routier and Jean-Yves Merour

Volume 4, Issue 3, 2007

Page: [198 - 202] Pages: 5

DOI: 10.2174/157017807780737291

Price: $65


New 1,5-Dihydro-4-(3,4,5-trimethoxyphenyl)-3H-furo[3,4-b]carbazol-3-ones were synthesized via a key Diels-Alder reaction under microwave irradiation. Two routes were investigated to generate the dienoic precursors. Both started from 3-formylindole, which was used in a six steps synthesis to obtain the complex heterocycle. The use and removal of indolic protective groups such as t-Boc and benzenesulfonyl have been studied. The Diels- Alder reaction generating the carbazole ring was optimised under either thermal conditions or microwave irradiation.

Keywords: Indole, carbazole, Diels-Alder, microwave, lignans

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