title: Lawesson's reagent-initiated domino reaction of aminopropenoyl cyclopropanes: synthesis of thieno[3,2-c]pyridinones.
abstract: A convenient and efficient synthesis of substituted 2,3-dihydrothieno[3,2-c]pyridin-4(5H)-ones has been developed and relies upon a domino reaction of dimethylaminopropenoyl cyclopropanes initiated by Lawesson's reagent. A mechanism involving regioselective thionation, ring-enlargement, and an intramolecular aza-cyclization sequence is proposed. This protocol was utilized as a one-pot route to thieno[3,2-c]pyridin-4(5H)-ones with DDQ as an oxidant.
authors.affiliation: Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, China.
authors.forename: Peng
authors.initials: P
authors.lastname: Huang
authors.forename: Rui
authors.initials: R
authors.lastname: Zhang
authors.forename: Yongjiu
authors.initials: Y
authors.lastname: Liang
authors.forename: Dewen
authors.initials: D
authors.lastname: Dong
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D003521:Cyclopropanes / Q000737:chemistry*; D015394:Molecular Structure; D011728:Pyridones / Q000138:chemical synthesis*
chemical_list: D000475:Alkenes; D003521:Cyclopropanes; D011728:Pyridones; C013658:propylene