April 28, 2024

Mohammad Abbasi

Academic Rank: Associate professor
Address:
Degree: Ph.D in organic chemistry
Phone: 09173096425
Faculty: Faculty of Nano and Biotechnology

Research

Title
Investigation of new methods for synthesis of benzothioamides using benzyl mercaptans or halides
Type Thesis
Keywords
كاتاليست يوروفتال (8020)، تيوآميد، كاتاليست هاي آلي-فلزي، تيول ها، آمين ها، بنزيل هاليدها، بنزيل دي سولفيدها
Researchers naser zarin derakht (Student) , Mohammad Abbasi (Primary advisor) , Najmeh Nowrouzi (Advisor)

Abstract

Background: There are several procedures based on different strategies reported in the literature for thioamides synthesis which include three component coupling reactions of aldehydes or ketones, amines, and elemental sulfur (Willgerodt-Kinder reactions), thionation of amides using Lawesson’s reagent or P4S10, thiolysis of iminium salts and nitriles with H2S, NaSH or (NH4)2S, Friedel-Crafts reaction with metal thiocyanates, thioacylation of amines using alkyldithioic acids, a four-component condensation of isocyanides, CS2, primary amines and aldehydes, and reduction of N-arylimino-1,2,3-dithiazoles by LiAlH4. In addition, reaction of dibenzyl disulfides with amines under oxidative conditions in the presence of suitable catalysts including I2 and S8 as recent strategy has been employed. In theory, when a molecule is synthesized from disulfide, it may be possible to synthesize it by starting from the corresponding thiol under oxidative conditions. In this line, an aerobic oxidation condition has been developed by Wang et. al. using CuCl2 and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) under O2 atmosphere for the synthesis of thioamides from thiols and amines in toluene. Wang's method is more valuable than disulfide-based methods because disulfides are usually obtained by oxidation of the corresponding thiols. In addition, the use of aerobic conditions in oxidative reactions is itself an advantage. Despite these advantages, this method has drawbacks and suffers from disadvantages such as the need for O2 and its equipment and the need for a significant amount of expensive TBD. We proposed three different strategies for synthesizing these compounds: 1. Treatment of benzyl mercaptans with amines in the presence of industrial Europhtal (8020) catalyst. 2. The one-pot reaction of benzyl halides with thiourea and various amines in DMSO in the presence of Europhtal (8020) catalyst. 3. The reaction of benzylic halides, Na2S2O3.5H2O and amines in DMSO without needing any additi