ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Study on synthesis of some substituted N-propargyl isatins by propargylation reaction of corresponding isatins using potassium carbonate as base under ultrasound- and microwave-assisted conditions

Nguyen Minh Tri, Nguyen Dinh Thanh, Luong Ngoc Ha, Dang Thi Tuyet Anh, Vu Ngoc Toan, and Nguyen Thi Kim Giang

Department of Toxicological Chemistry and Radiation, Institute for Advanced Technology (Academy of Military Science and Technology, Vietnam), Ha Noi, Vietnam

E-mail: nguyendinhthanh@hus.edu.vn

Received: 26 February 2021  Accepted: 10 May 2021

Abstract:

Substituted N-propargyl isatins were synthesized by S_N2 reaction of corresponding substituted isatins with propargyl bromide in the presence of anhydrous K₂CO₃ as base. We reported about study on systematically synthesis of these compounds using heating procedures under different reaction conditions, including microwave-assisted heating conditions at power of 100 W (Procedure A), conventional heating conditions in water bath at 50 °C in acetonitrile (Procedure B), and conventional heating conditions in water bath at 50 °C in DMF (procedure C). The best procedure A was deduced based on the investigations on the reaction conditions. Almost all substituted N-propargyl isatins were new, except compounds with R of H, 5-Me, 5-Cl and 5-Br substituents. The structures of the obtained compounds were confirmed by the modern spectroscopic methods.

Keywords: 1-Alkyne; Isatins; Propargyl bromide; N-propargylation; Microwave-assisted; Ultrasound-assisted

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-021-01697-6

Chemical Papers 75 (9) 4793–4801 (2021)