One-Pot Synthesis of Pyrrolo[3,2-f]- and Pyrrolo[2,3-h]quinoline Derivatives: Observation of an Unexpected Mechanistic Pathway

Abstract

One-pot synthesis of pyrrolo[3,2-f]- and pyrrolo[2,3-h]quinolines were obtained starting from substituted 5-aminoindoles, benzaldehydes, and phenylacetylenes in the presence of La(OTf)₃ as a catalyst in good yields. The indole moiety in 5-aminoindole is believed to be mainly responsible for the observation of unexpected mechanistic pathway to the formation of pyrrolo[2,3-h]quinoline.

pyrroloquinoline - one-pot synthesis - 5-aminoindole - Lewis acid

References and Notes

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The CCDC deposition number for compound 4a is 796984. Formula: C₂₆H₂₂N₂. Unit cell parameters: a = 7.3436 (16), b = 11.1808 (17), c = 12.467 (3), α = 99.382 (15), β = 102.495 (19), γ = 94.742 (15), space group P-1. The CCDC deposition number for compound 5g is 796985. Formula: C₅₈H₅₆N₄. Unit cell parameters: a = 8.3864 (9), b = 13.2389 (14), c = 21.6848 (19), α = 80.350 (8), β = 82.567 (8), γ = 82.391 (9), space group P-1.

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