A New Method for the Synthesis of Functionalized 5-Hydroxy-1,5-dihydro-2H-pyrrol-2-one: Reaction of an Enamine, Derived from Addition of a Secondary­ Amine to Dibenzoylacetylene, with an Arylsulfonyl Isocyanate

Abstract

An effective route to novel 5-hydroxy-1,5-dihydro-2Hpyrrol-2-one is described which involves the reaction of an enamine, derived from addition of a secondary amine to dibenzoylacetylene, with an arylsulfonyl isocyanate.

3-Benzamido-1-benzoyl-1H-pyrrol-2(5H)-one

“…For the synthesis of 1,5-dihydro-2H-pyrrol-2-ones, see: Gao et al (1997); Alizadeh et al (2006); Nedolya et al (2002); Mušič et al (1998).…”

Novel Synthesis of 5-Oxo-2-thioxo-2,5-dihydro-3-thiophenecarboxylate Derivatives in Non-Aqueous Medium

“…catalyst in iPrOH. Earlier treatment of amine and its derivatives like dialkylacetylendicarboxylate and isocyante by Alizadeh et al [18,19] at room temperature led to the formation of maleimide derivatives. The reaction product was separated using ethyl acetate as organic solvent [20].…”

One-Pot Synthesis of Arylsulfonamides and Azetidine-2,4-diones via Multicomponent Reaction of an Amine, an Acetylenic Compound, and an Arylsulfonyl Isocyanate

“…[14][15][16][17][18][19] In the context of our ongoing studies on heterocyclic synthesis mediated by enamine intermediates, the possibility of trapping the 1:1 intermediate 5, formed between an acetylenecarboxylate 2 and a primary or secondary amine 1, with an arysulfonyl isocyanate 3 appeared attractive from the viewpoint of devising a novel multicomponent reaction (MCR). Although the trapping of the 1:1 intermediate formed between dibenzoylacetylene or dialkyl acetylenedicarboxylate and amines with arylsulfonyl isocyanate has been studied in detail by our research group, [20][21][22] trapping of the initially formed 1:1 intermediate between primary amines and alkyl propiolates has not been reported.…”

“…Compounds 4 apparently result from the initial addition of an amine to the acetylenic system and subsequent attack of the resulting reactive enamine 5 on the arylsulfonyl isocyanate [20][21][22][23][24] to yield a betaine 6, which under hydrogen shift produce 4 (Scheme 1).…”

“…Although we have not established the mechanism of the reaction of the enamine derived from the addition of Et 2 NH to 2a and 3 in an experimental manner, a possible explanation is proposed in Scheme 2. Compound 7 appar-ently results from the initial addition of Et 2 NH to the acetylenic system and subsequent attack of the resulting reactive enamine 8 to the arylsufonyl isocyanate [20][21][22][23][24] to yield betaine 9, which apparently cyclizes, under the reaction condition employed with loss of methanol to produce the malonimide 7.…”