One-pot synthesis of ortho-hydroxycinnamate esters

Abstract

under the supervision of Associate Professor Trond Vidar Hansen. Financial support from Quota Programme and The Research Council of Norway is gratefully acknowledged. It is a pleasure to thank all of you who made this thesis possible. Firstly, I sincerely thank my supervisor, Associate Professor Trond Vidar Hansen for giving me the opportunity to start on this interesting project, and for his help, availability, advice, and guidance during my stay in his research group. I would like to thank Professor Lars Skattebøl for his useful advice, guidance, helpful discussions, and proofreading my manuscripts throughout these years. Also I would like to thank Professor Arne Jørgen Aasen for sharing his knowledge and proofreading my thesis. I am grateful to all members of Trond Vidar Hansen's group, the Department of Pharmaceutical Chemistry, my colleagues, and especially Alexandra Gade and Øyvind Jacobsen, and also of the technical staff for social and scientific contribution. Lastly, I would like to thank my wife, Sylvia Antoun, for her love, encouragement and patience over these years.

Synthesis of Substituted Coumarins and 2‐Quinolinones by Cycloisomerisation of (Hydroxy/aminophenyl)propargyl Alcohols

“…1 H NMR (300 MHz, [D 6 ]DMSO): δ = 11.7 (s, 1 H), 7.9 (d, J = 9 Hz, 1 H), 7.6 (d, J = 9 Hz, 1 H), 7.5 (t, J = 9 Hz, 1 H), 7.3 (d, J = 9 Hz, 1 H), 7.1 (t, J = 9 Hz, 1 H), 6.5 (d, J = 9 Hz, 1 H) ppm. 13 6,7-Dimethoxyquinolin-2(1H)-one (5c): [25] [26] 458 mg, 90 % yield. White solid.…”

“…[11] [12] 8-tert-Butyl-2H-chromen-2-one (2c): [13] 334 mg, 83 % yield. and H 2 O (90 mg, 5 mmol) were added to a solution of 8 (357 mg, 1 mmol) in CH 3 CN (6 mL).…”

“…ppm 13. C NMR (75 MHz, [D 6 ]DMSO): δ = 159.4, 152.1, 145.1, 136.6, 129.1, 126.9, 124.0, 119.1, 115.2, 34.4, 29.4 ppm.…”

“…(q, J = 3.05 Hz, 2 H), 1.5 (t, J = 3.5 Hz, 3 H) ppm 13. C NMR (50 MHz, CDCl 3 ): δ = 162.0, 150.3, 145.8, 137.4, 130.0, 129.5, 129.3, 129.2, 128.8, 128.7, 124.87, 124.81, 114.0, 61.9, 14.7 ppm.…”

“…463 mg, 85 % yield. H NMR (300 MHz, CDCl 3 ): δ = 7.65 (d, J = 8.1 Hz, 1 H), 7.61 (d, J = 7.9 Hz, 2 H), 7.3 (t, J = 7.6 Hz, 1 H), 7.2 (d, J = 7.9 Hz, 2 H), 7.1 (t, J = 7.6 Hz, 1 H), 7.0 (d, J = 7.6 Hz, 1 H), 6.6 (s, 1 H), 5.4 (s, 1 H), 4.2 (q, J = 7.3 Hz, 2 H), 2.3 (s, 3 H), 2.1 (s, 3 H), 1.3 (t, J = 7.3 Hz, 3 H) ppm 13. R f = 0.3 (EtOAc/hexanes, 7:3).…”