title: Synthesis of 3-Sulfonylamino Quinolines from 1-(2-Aminophenyl) Propargyl Alcohols through a Ag(I)-Catalyzed Hydroamination, (2 + 3) Cycloaddition, and an Unusual Strain-Driven Ring Expansion.
abstract: We describe herein a silver-catalyzed conversion of 1-(2-aminophenyl)-propargyl alcohols to 4-substituted 3-tosylaminoquinolines using TsN3 as an amino surrogate. Controlled reactions reveal the pathway consisting of Ag(I)-catalyzed 5-exo-dig cyclization, catalyst-free (2 + 3) cycloaddition, and ring-expansive rearrangement via nitrogen expulsion. As a support study, we show that the cyclic enamines in similar conditions produce amidines via a C-C bond migration.
authors: Yalla Kiran
authors: YK
authors: Kumar
authors: ∥Academy of Scientific and Innovative Research, New Delhi 110001, India.
authors: Gadi Ranjith
authors: GR
authors: Kumar
authors: Thota Jagadeshwar
authors: TJ
authors: Reddy
authors: §X-ray Crystallography Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
authors: Balasubramanian
authors: B
authors: Sridhar
authors: ∥Academy of Scientific and Innovative Research, New Delhi 110001, India.
authors: Maddi Sridhar
authors: MS
authors: Reddy
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D061565:Cycloaddition Reaction; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D012834:Silver / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D020005:Propanols; D011804:Quinolines; D013438:Sulfhydryl Compounds; D012834:Silver; C028255:propargyl alcohol