In situ vinylindole synthesis: Diels–Alder reactions with N-phenylmaleimides, 1-tetralones and 4-chromanones to give annulated tetrahydrocarbazoles

Abstract

An acid-catalyzed condensation of indole 4 with 1-tetralones 5a–f formed a vinylindole which reacted in situ with N-phenylmaleimides 7a–g. This cascade of condensation and Diels–Alder reaction was performed in IPA (isopropyl alcohol) and in presence of p-TsOH (p-toluenesulfonic acid) at reflux to produce annulated tetrahydrocarbazoles 8a–g and 10a–e. Similarly, 9a–g were synthesized by substituting 4-chromanone 6 for 5a–f. The 1-tetralone derived products 8a–g and 10a–e were obtained in higher yields (19–79%) compared to 4-chromanone derived 9a–g (6–28%), likely due to additional side reactions in case of chromanones. To establish the structure and stereochemistry of products, the crystal structure of 10c was obtained, confirming endo-Diels–Alder addition.