Mechanistic Studies on the Three Component Synthesis of Tetrahydrobenzo[ b]pyran Catalyzed by Agar

Asheri, Osman; Habibi‐Khorassani, Sayyed Mostafa; Shahraki, Mehdi

doi:10.2174/2213337202666150716171241

Cited by 6 publications

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“…Lactic acid (HL) is considered as a top 12 biobased platform molecule and may serve as a useful precursor chemical for producing green solvents and polymers [36,37] with wide usage in pharmaceuticals, cosmetics and food packaging [38,39]. In continuation of our ongoing programme in the kinetics of multi-component reactions [40][41][42][43][44][45][46][47][48][49][50], here we investigated the kinetics and mechanism of the reactions between para-substituted anilines 1 and dimethyl acetylenedicarboxylate (DMAD) (2) with benzaldehyde derivatives 3 for the formation of 3,4,5-substituted furan-2(5H)-ones using HL as an efficient catalyst in ethanol at ambient temperature, with good yields. Synthetic details of this reaction have been published earlier by Maghsoodlou and co-workers [51] (see Figure 1).…”

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confidence: 99%

A Study on the Kinetics and Mechanism of the One-Pot Formation of 3,4,5-Substituted Furan-2(5H)-Ones in the Presence of Lactic Acid: Effect of Different Substituents

Asheri

Habibi‐Khorassani

Shahraki

2018

Progress in Reaction Kinetics and Mechanism

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The kinetics of the reaction between para-substituted anilines and dimethyl acetylenedicarboxylate (DMAD) with derivatives of benzaldehyde for the one-pot formation of 3,4,5-substituted furan-2(5H)-ones in the presence of lactic acid as a catalyst have been studied spectrophotometrically at different temperatures. A mechanism involving four steps was proposed for the reactions, all of which followed second-order kinetics. The partial orders with respect to substituted aniline and DMAD were one and one and the reactions revealed zeroorder kinetics for benzaldehyde and its derivatives. Changing of substituents on benzaldehyde left rates of reaction unaffected. However, various substituents on aniline showed that para electron-withdrawing groups decreased the rate of reaction. According to investigation of an isokinetic relationship, a common mechanism exists for all studied substituents and a general mechanism can be formulated. Kinetic values (k and E a) and associated activation parameters (ΔG ‡ , ΔS ‡ and ΔH ‡) of the reactions were determined.

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