TAILIEUCHUNG - Ultrasound-accelerated arylthiomethylation of indole via multicomponent reaction in water catalyzed by acetic acid

Multicomponent reactions (MCRs) play an important role to create the molecular complexity in a one-step process. Based on the mechanism and process of Mannich-type reactions in the synthesis of Grammin, arylthiomethylation reactions of indole were performed by using three components: indole, p-thiocresol and a solution of formaldehyde (36%) under two activation conditions, . magnetic stirring and ultrasonic irradiation. The main product, 3-(p-tolylthiomethyl)-1H-indole, was obtained in a moderate yield (54%) under short irradiation (40 minutes) by probe sonicator. | Science & Technology Development, Vol 20, 2017 Ultrasound-accelerated arylthiomethylation of indole via multicomponent reaction in water catalyzed by acetic acid Luu Thi Xuan Thi University of Science, VNU-HCM Pham Quang Vinh Le Hong Phong upper secondary school-Dong Nai (Received on June 5th 2016, accepted on April 10th2017 ) ABSTRACT Multicomponent reactions (MCRs) play an important role to create the molecular complexity in a one-step process. Based on the mechanism and process of Mannich-type reactions in the synthesis of Grammin, arylthiomethylation reactions of indole were performed by using three components: indole, p-thiocresol and a solution of formaldehyde (36%) under two activation conditions, . magnetic stirring and ultrasonic irradiation. The main product, 3-(p-tolylthiomethyl)-1H-indole, was obtained in a moderate yield (54%) under short irradiation (40 minutes) by probe sonicator. Keywords: arylthiomethylation, ultrasound irradiation, acetic acid, and indole INTRODUCTION Mannich reaction classified into multicomponent reactions (MCRs), has been fairly extensively investigated, while there are few studies using thiols in place of amines for Mannich-type reaction, namely alkylthiomethylation and arylthiomethylation. The latter has been used widely in organic chemistry, especially in total synthesis of natural products, . sesquiterpenes and antibiotics [1-5]. Formaldehyde is a very active substrate frequently used in three-component reactions in order to generate active methylene transition compounds (or methides) via the methylenation of electron-rich carbons with formaldehyde. Subsequently, these active methylene intermediates were trapped by ,βunsaturated ketones [1], ,β-unsaturated esters [2], Trang 80 lactams [3, 4, 6], thiols [5, 7], indole [7, 8], and polyarenes [9]. In pursuit of our work on the analogue of the Mannich reaction, we report the arylthiomethylation involving indole, p-thiocresol and the solution .

• Hoá học
• Ultrasound accelerated arylthiomethylation
• Mannich type reactions
• Magnetic stirring and ultrasonic irradiation
• The mechanism and process
• Mannich type reactions in the synthesis