✦ LIBER ✦

A novel synthesis of 3-nitroindoles via electrocyclization of 2,3-(dialk-1-enyl)-4-nitropyrroles

✍ Scribed by Ronald ten Have; Albert M van Leusen

Book ID: 104208313
Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 487 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)10405-7

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✦ Synopsis

3-Nitroindoles (10) are prepared in good yields via a thermal 6n-electrocyclization of 2,3-(dialkenyl)-4-nitropyrroles (4) in nitrobenzene, a solvent which causes in situ aromatization of the initially formed dihydroindoles (8). The corresponding reaction of 2-alkenyl-3-alkadienyl-4-nitropyrroles (5) also leads to 3-nitroindoles (11), however, now together with 3-nitrotetrahydroindole derivatives (12). The latter compounds are formed by a tandem 6n-electrocyclization -intramolecular Diels-Alder reaction, and are the predominant (or only) products when nitrobenzene is replaced by triglyme.

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