title: Parallel syntheses of eight-membered ring sultams via two cascade reactions in water.
abstract: From vinyl sulfonamides as precursors to vinyl sulfonamide epoxides, two cascade reaction protocols were developed to synthesize eight-membered ring sultams in water. These protocols employ intermolecular Michael addition by NaOH or NaHS in water, followed by rapid proton transfer and intramolecular 8-endo-tet epoxide ring-opening to give medium-size sultams selectively in one-pot. Novel core structures and high synthetic efficiency make these cascade reactions highly suitable for sultam library production. Both reactions proceeded well and afforded the respective sultams in good yields under environmentally friendly conditions.
authors.affiliation: Pharmacy School, Jiangsu University , Xuefu Road 301, Zhenjiang City, Jiangsu, 212013, China.
authors.forename: Tao
authors.initials: T
authors.lastname: Ji
authors.forename: Yanjie
authors.initials: Y
authors.lastname: Wang
authors.forename: Min
authors.initials: M
authors.lastname: Wang
authors.forename: Ben
authors.initials: B
authors.lastname: Niu
authors.forename: Ping
authors.initials: P
authors.lastname: Xie
authors.forename: Charles U
authors.initials: CU
authors.lastname: Pittman
authors.forename: Aihua
authors.initials: A
authors.lastname: Zhou
mesh_terms: D020650:Combinatorial Chemistry Techniques; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
chemical_list: D004852:Epoxy Compounds; D013449:Sulfonamides; C480101:beta-sultam; C440389:vinyl sulfonamide; D014867:Water