Dynamic covalent chemistry of disulfides offers a highly efficient synthesis of diverse benzofused nitrogen-sulfur heterocycles in one pot.
The thiol-disulfide dynamic interchange reaction mediated by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was extensively studied. By this synthetic method sulfides can be prepared successfully within seconds in high yields at room temperature from stable and readily available disulfides and an alkylating agent. The method was further demonstrated to efficiently produce benzofused nitrogen-sulfur heterocycles with high skeletal diversity in a one-pot process.
Zhu
Ning
N
Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Xuanwu District, Beijing 100050, China.
Zhang
Fa
F
Liu
Gang
G
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D004220:Disulfides / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D054852:Small Molecule Libraries; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry*
D019086:Bridged Bicyclo Compounds, Heterocyclic; D004220:Disulfides; D006571:Heterocyclic Compounds; D054852:Small Molecule Libraries; D013455:Sulfur; C031033:1,8-diazabicyclo(5.4.0)undec-7-ene; D009584:Nitrogen