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One-Pot Synthesis of 4-(Alkylamino)-1-(arylsulfonyl)-3-benzoyl-1,5- dihydro-5-hydroxy-5-phenyl-2H-pyrrol-2-ones via a Multicomponent Reaction

✍ Scribed by Abdolali Alizadeh; Atieh Rezvanian; Long-Guan Zhu

Publisher
John Wiley and Sons
Year
2007
Tongue
German
Weight
247 KB
Volume
90
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

An effective route to novel 4‐(alkylamino)‐1‐(arylsulfonyl)‐3‐benzoyl‐1,5‐dihydro‐5‐hydroxy‐5‐phenyl‐2__H__‐pyrrol‐2‐ones 10 is described (Scheme 2). This involves the reaction of an enamine, derived from the addition of a primary amine 5 to 1,4‐diphenylbut‐2‐yne‐1,4‐dione, with an arenesulfonyl isocyanate 7. Some of these pyrrolones 10 exhibit a dynamic NMR behavior in solution because of restricted rotation around the CN bond resulting from conjugation of the side‐chain N‐atom with the adjacent α,β‐unsaturated ketone group, and two rotamers are in equilibrium with each other in solution (10 ⇌ 11; Scheme 3). The structures of the highly functionalized compounds 10 were corroborated spectroscopically (IR, ^1^H‐ and ^13^C‐NMR, and EI‐MS), by elemental analyses, and, in the case of 10a, by X‐ray crystallography. A plausible mechanism for the reaction is proposed (Scheme 4).

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