A stable analogue of indole-2,3-quinodimethane: synthesis and Diels?Alder reaction of 2-methoxycarbonyl-4-[(p-methoxyphenyl)sulphonyl]-2,4-dihydropyrrolo[3,4-b]indole
โ Scribed by Soa, Chin-Kang; Chuang, Kuang-Sein; Young, Jenn-Jonn
- Book ID
- 120992638
- Publisher
- The Royal Society of Chemistry
- Year
- 1984
- Tongue
- English
- Weight
- 179 KB
- Volume
- 0
- Category
- Article
- ISSN
- 0022-4936
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๐ SIMILAR VOLUMES
The N-phenylsulfonyl derivative (2) of the previously unknown fused heterocycle 4Hfuro[3,4-blindole is synthesized from indole-3-carboxaldehyde (2) in 28% yield and undergoes a Diels-Alder reaction with benzyne to give 5H-benzo[b]carbazole (11) in -33% yield after deoxygenation and deprotection.
Inverse electron-demand Diels-Alder reactions of 1,2,4-triazines, where the dienophile is present in a sidechain tethered to the azadiene, can proceed with remarkable facility, leading to a variety of condensed pyridines (Scheme 1). Several recent publications from our laboratory have served to illu