Microwave-assisted multi-step synthesis of novel pyrrolo-[3,2-c]quinoline derivatives

Abstract

A new approach for the synthesis of original substituted pyrrolo-[3,2-c]quinoline derivatives using microwave-assisted chemistry is described. The use of microwave activation in this synthesis resulted in high yielding and clean steps. The key step for introducing diversity is the amination or the Pd-catalyzed cross-coupling of an imidoyl chloride derivative, obtained in a straightforward manner and in good yield.

Novel 1H-Pyrrolo[3,2-c]quinoline Based 5-HT6 Receptor Antagonists with Potential Application for the Treatment of Cognitive Disorders Associated with Alzheimer’s Disease

“…The starting nitrobenzaldehyde, tosylamine, and methyl acrylate reacted in the presence of DABCO and titanium isopropoxide, in isopropanol, under the aza-Bayliss−Hillman reaction conditions, to yield the unsaturated β-aminoester 1. 19 Subsequently, compound 1 was treated with allyl bromide in a biphasic system to give diene 2. The latter was submitted to a ring-closing metathesis reaction, using Grubbs second-generation catalyst, in refluxing dichloromethane for 30 min, to yield pyrroline 3.…”

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“…They also used this methodology in a stereoselective manner: with the use of chiral amines they reached ee values of up to 74 % 139b. Benakki et al modified this method by using DABCO instead of 3‐HQD but obtained “olefinic products” in lower yields 139c. Lamaty et al139d replaced the Ar 2 SO 2 substituent in the sulfonamide with the 2‐trimethylsilylethanesulfonyl (SES) group.…”

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“…Both functionalities are crucial for substrate synthesis and the former provides acidification for the final elimination step. This methodology was later adapted to the synthesis of pyrrolo-[3,2-c]quinolines [39,40]. …”