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Sulfur-Mediated Decarboxylative Coupling of 2-Nitrobenzyl Alcohols and Arylacetic Acids

Khang X. Nguyen, Duyen K. Nguyen, Phuc H. Pham, Ha V. Le, Tung T. Nguyen, Nam T. S. Phan*

*Department of Chemical Engineering, HCMC University of Technology, VNU-HCM, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City, Vietnam, Email: ptsnamhcmut.edu.vn

K. X. Nguyen, D. K. Nguyen, P. H. Pham, H. V. Le, T. T. Nguyen, N. T. S. Phan, Synlett, 2020, 31, 1112-1116.

DOI: 10.1055/s-0040-1707113


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Abstract

The condensation of 2-nitrobenzyl alcohols with arylacetic acids provides substituted quinazolines under mild conditions in the presence of urea as a nitrogen source, elemental sulfur as a promoter, DABCO as a base, and DMSO as a solvent. The reaction tolerates functionalities such as chloro, fluoro, trifluoromethyl, thienyl, and indolyl groups.

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Details

The document details a novel method for synthesizing substituted quinazolines through the sulfur-mediated decarboxylative coupling of 2-nitrobenzyl alcohols and arylacetic acids. This process uses urea as a nitrogen source, elemental sulfur as a promoter, DABCO as a base, and DMSO as a solvent. The method is notable for its compatibility with various functional groups, including chloro, fluoro, trifluoromethyl, thienyl, and indolyl groups, and does not require transition metals. The reaction conditions were optimized, revealing that an excess of elemental sulfur and the use of DMSO as a solvent were crucial for high yields. The study also explored the scope of the reaction with different benzylic coupling partners and phenylacetic acids, demonstrating good yields with both electron-rich and electron-deficient substrates. Mechanistic studies suggested the formation of a bisimine intermediate through radical pathways. This method offers a more atom-economical and versatile approach to synthesizing complex N,N-heterocycles under mild conditions, with potential applications in the preparation of biologically active compounds. The research was supported by the Vietnam National University Ho Chi Minh City.


Key Words

quinazolines, nitrobenzyl alcohols, arylacetic acids, sulfur, cyclocondensation, decarboxylation


ID: J72-Y2020