Microwave-Assisted Three-Component Reaction for the Synthesis of Pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-ones

Abstract

Pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-ones can be obtained by a microwave-assisted three-component reaction between 2-aminopyridines, isocyanides, and 2-carboxybenzaldehydes under acidic conditions.

heterocycles - lactams - multicomponent reaction - Ugi reaction - isocyanides

References

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6

Mert-Balci, F.; Beifuss, U. unpublished results.

Other approaches to this and related ring systems:

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7d After completing the experimental work we learned about a similar domino process yielding pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-ones under different reaction conditions: Meng T. Zhang Z. Hu D. Lin L. Ding J. Wang X. Shen J. J. Comb. Chem.  2007,  9:  739 

8a

X-ray crystal structure analysis for 6n: formula C₂₄H₂₁N₃O₃, M = 399.44, orange crystal 0.10 × 0.03 × 0.02 mm^³, monoclinic, space group P2₁/n, a = 22.673(2), b = 7.2566(7), c = 24.348(2) Å, β = 107.4740(10)˚, V = 3821.1(6) Å^³, ρ_calcd = 1.389 µg/m^³, absorption coefficient µ = 0.093 mm^-¹, Z = 8, reflections collected 41880, θ_max = 28.49˚, independent reflections 9106 [R _int = 0.0678], final R1 [I > 2σ(I)] = 0.0454, wR2 [I > 2σ(I)] = 0.0977, R1 (all data) = 0.1016, wR2 (all data) = 0.1172, GOF = 1.016, extinction parameter = 0.0012(2), largest diff. peak and hole 0.252 and -0.249
eÅ^-³.

8b

X-ray data were collected at 100(2) K on an INCOATEC Microsource device with mirror-monochromated Mo-Kα radiation (λ = 0.71073 Å). The device is equipped with a SMART APEX II area detector. The data were integrated with SAINT⁹ and an empirical absorption correction (SADABS)^¹0 was applied. The structure was solved by using direct methods with SHELXS-97 and refined by full-matrix least-squares on F ^² for all data with SHELXL-97.^¹¹-¹³ All non-hydrogen atoms were refined with anisotropic displacement parameters. A riding model with idealized geometry was employed for all hydrogen atoms. CCDC-674626 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

9

SAINT-NT, Bruker AXS Inc., Madison, Wisconsin, USA, 2006.

10

Sheldrick, G. M. SADABS 2006/4, University of Göttingen, Germany, 2006.

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