New efficient synthesis of 1H-imidazo-[4,5-c]quinolines by a sequential Van Leusen/Staudinger/aza-Wittig/carbodiimide-mediated cyclization

A new efficient synthesis of multisubstituted 1H-imidazo-[4,5-c]quinoline derivatives via sequential van Leusen/Staudinger/aza-Wittig/carbodiimide-mediated cyclization was developed. Azides 4, obtained from Van Leusen reaction of 2-azidobenzaldehyde 1, amine 2 and TosMIC (tosylmethyl isocyanide) 3,...

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Bibliographic Details
Published in:Tetrahedron 2018-12, Vol.74 (50), p.7186-7192
Main Authors: Guan, Zhi-Rong, Liu, Zi-Ming, Ding, Ming-Wu
Format: Article
Language:English
Subjects:
1H-imidazo-[4,5-c]quinoline
Aza-Wittig reaction
Carbodiimide
Staudinger reaction
Van Leusen reaction
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Summary:A new efficient synthesis of multisubstituted 1H-imidazo-[4,5-c]quinoline derivatives via sequential van Leusen/Staudinger/aza-Wittig/carbodiimide-mediated cyclization was developed. Azides 4, obtained from Van Leusen reaction of 2-azidobenzaldehyde 1, amine 2 and TosMIC (tosylmethyl isocyanide) 3, reacted with triphenyl phosphine to produce iminophosphorane 5. A tandem aza-Wittig reaction of iminophosphorane 5 with isocyanate generated 1H-imidazo-[4,5-c]quinoline 7 through carbodiimide intermediate 6 in moderate to good yield. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.10.052