Thiosalicylic Acid Catalyzed Multicomponent Reactions: Microwave-Assisted Synthesis of New Extended Angular Fused Azaheterocycles

Abstract

A new, efficient and convenient approach to the synthesis of new extended angular fused aza-heterocycles including dibenzacridine and naphth[2,3-a:2′,3′-j]acridine units with good luminescent properties is described. The multicomponent reactions (MCRs) were conducted by reacting readily available and inexpensive starting materials using thiosalicylic acid as a catalyst under microwave irradiation. A total of 14 examples were examined, and a broad substrate scope and high overall yields (72-89%) were revealed.

Key words

microwave irradiation - multicomponent reaction - dibenzacridines - naphth[2,3-a:2′,3′-j]acridines

References

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15

Single-crystal growth was carried out in N,N-dimethyl­-formamide at room temperature. X-ray crystallographic analysis was performed with a Siemens SMART CCD and a Semens P4 diffractometer. Crystal data for 4h (CCDC 793729): C₂₈H₁₉NO₂; crystal dimensions 0.18 × 0.12 × 0.10 mm; monoclinic; space group P2 (1)/n; a = 9.4920 (11) Å, b = 11.2767 (16) Å, c = 18.883 (2) Å, α = 90˚, β = 102.650 (2)˚, γ = 90˚^; V = 1972.1 (4) Å^³; Mr = 401.44; Z = 4; Dc = 1.352 g/cm^³; λ = 0.71073 Å; µ (MoK_α) = 0.085 mm^-¹; F(000) = 840, R ₁ = 0.1032, wR ₂ = 0.0544.