title: Regioselective synthesis of functionalized dihydroisoquinolines from o-alkynylarylaldimines via the Reformatsky reaction.
abstract: A novel approach for the synthesis of functionalized 1,2-dihydroisoquinolines from o-alkynylarylaldimines via the Reformatsky reaction without the aid of an external Lewis acid has been described. The chemistry involves the dual role of the Reformatsky reagent which has been generated in situ in the reaction. We propose that one molecule of the Reformatsky reagent is being utilised for the activation of alkynes, whereas the second molecule acts as a nucleophile on the iminium carbon. This synthetic pathway has high functional group tolerance, and can be utilized on a gram scale. The proposed mechanistic pathway is well supported by the control experiments. The 1,2-dihydroisoquinoline derivatives showed up to 90% inhibition of the strand transfer activity of the HIV integrase enzyme.
authors.affiliation: Special Centre for Molecular Medicine, Jawahar Lal Nehru University, New Delhi-110067, India. vtandon@mail.jnu.ac.in vibhadelhi6@gmail.com.
authors.forename: Tohasib Yusub
authors.initials: TY
authors.lastname: Chaudhari
authors.affiliation: Department of Chemistry, University of Delhi, New Delhi-110007, India.
authors.lastname: Urvashi
authors.affiliation: Syngene International Ltd, Biocon Park, Plot # 2 & 3, Phase IV, Bommasandra, Jigani Link Road, Bengaluru, Karnataka-560099, India.
authors.forename: Sandeep K
authors.initials: SK
authors.lastname: Ginotra
authors.affiliation: Department of Chemistry, University of Delhi, New Delhi-110007, India.
authors.forename: Pooja
authors.initials: P
authors.lastname: Yadav
authors.affiliation: Department of Chemistry, University of Delhi, New Delhi-110007, India.
authors.forename: Gulshan
authors.initials: G
authors.lastname: Kumar
authors.affiliation: Special Centre for Molecular Medicine, Jawahar Lal Nehru University, New Delhi-110067, India. vtandon@mail.jnu.ac.in vibhadelhi6@gmail.com and Department of Chemistry, University of Delhi, New Delhi-110007, India.
authors.forename: Vibha
authors.initials: V
authors.lastname: Tandon
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D007097:Imines / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; C109853:G 1617; D007097:Imines; D007546:Isoquinolines