Three‐Component Synthesis of 2‐Substituted Thiobenzoazoles Using Tetramethyl Thiuram Monosulfide (TMTM) as Thiocarbonyl Surrogate
Xi Wang, Chun‐Yan Wu, Yuesheng Li, Zhi‐Bing Dong
Abstract
A metal‐free synthesis of 2‐benzyl/allyl‐substituted thiobenzoazoles was developed starting from tetramethyl thiuram monosulfide (TMTM) which served as thiocarbonyl surrogate. By using 2‐aminophenols (or 2‐aminothiophenols, or 1,2‐phenylenediamines) and TMTM as starting materials, 2‐mercaptobenzoazoles could be synthesized efficiently. The subsequent C–S bond formation with benzyl/allyl halides gave the final products (2‐benzyl/allyl‐substituted thiobenzoazoles) with good to excellent yields. The metal‐free conditions, inexpensive and easily available starting materials, and broad substrate scope are the advantageous features of this protocol.
Topics & Concepts
ChemistryHalideSubstrate (aquarium)Combinatorial chemistryOrganic chemistryPolymer chemistryGeologyOceanographySulfur-Based Synthesis TechniquesSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods