Synlett 2019; 30(09): 1073-1076
DOI: 10.1055/s-0037-1611804
letter
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Regioselective Heck–Suzuki–Miyaura Cascade Cyclization for the Synthesis of Trisubstituted Arylideneisoquinolinones

M. S. Asgari
a   School of Chemistry, University College of Chemistry, University of Tehran, Tehran, PO Box 14155-6455, Iran   Email: Parvizrashidi2@ut.ac.ir
,
R. Mirzazadeh
b   Biochemistry Department, Pasteur Institute of Iran, Pasteur Avenue, Tehran 1316943551, Iran
,
B. Larijani
c   Department of Medicinal chemistry, Facaulty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medicinal Sciences, Tehran, Iran   Email: Momahdavi@tums.ac.ir
,
P. Rashidi Ranjbar*
a   School of Chemistry, University College of Chemistry, University of Tehran, Tehran, PO Box 14155-6455, Iran   Email: Parvizrashidi2@ut.ac.ir
,
R. Rahimi
d   Department of Chemistry, Iran University of Science and Technology, Narmak, Tehran 16846-13114, Iran
,
M. Mahdavi*
c   Department of Medicinal chemistry, Facaulty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medicinal Sciences, Tehran, Iran   Email: Momahdavi@tums.ac.ir
› Author Affiliations
Further Information

Publication History

Received: 10 February 2019

Accepted after revision: 01 April 2019

Publication Date:
18 April 2019 (online)


Abstract

An Ugi four-component reaction was used to construct propargylamide starting materials for a subsequent domino Heck–Suzuki–Miyaura cross-coupling reaction to give derivatives of 4-benzylidene-1-oxo-3,4-dihydro-1H-isoquinoline.

Supporting Information

 
  • References and Notes

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  • 24 2-[(4E)-4-Benzylidene-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl]-2-(4-chlorophenyl)-N-cyclohexylacetamide (7a): Typical Procedure Ugi adduct 5a (0.5 mmol) was mixed with PhB(OH)2 (0.6 mmol), Na2CO3 (1.5 mmol), and Pd(OAc)2 (0.1 mmol) in 3:1 1,4-dioxane–H2O (6 mL), and the resulting solution was stirred at 80 °C under argon for 12 h. When the reaction was complete (TLC), the mixture was filtered through Celite, and the filtrate was diluted with H2O (10 mL) and EtOAc (10 mL). The combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure. The resultant crude product was purified by preparative TLC [silica gel, hexane–EtOAc (8:2)] to give a white solid; 79% yield; mp 200–202 °C. IR (KBr): 3274, 3074, 2929, 2853, 1639, 1293 cm–1. 1H NMR (500 MHz, DMSO-d 6): δ = 8.34 (d, J = 7.3 Hz, 1 H), 7.98 (d, J = 7.4 Hz, 1 H), 7.47 (d, J = 7.7 Hz, 2 H), 7.44–7.37 (m, 1 H), 7.33 (d, J = 7.8 Hz, 2 H), 7.31–7.24 (m, 4 H), 7.22–7.15 (m, 2 H), 7.08 (d, J = 7.4 Hz, 1 H), 6.58 (s, 1 H), 6.43 (s, 1 H), 4.40 (d, J = 13.0 Hz, 1 H), 3.69 (d, J = 13.0 Hz, 1 H), 3.63 (s, 1 H), 1.83–1.79 (m, 1 H), 1.78–1.73 (m, 1 H), 1.69–1.62 (m, 2 H), 1.54 (d, J = 11.4 Hz, 1 H), 1.30–1.06 (m, 5 H). 13C NMR (500 MHz, CDCl3): δ = 167.52, 163.50, 135.76, 135.26, 135.18, 132.59, 131.11, 131.04, 130.42, 130.31, 129.13, 129.09, 128.64, 128.57, 127.66, 126.33, 58.29, 51.53, 47.86, 32.22, 32.12, 25.13, 24.53, 24.45. Anal. Calcd for C30H29ClN2O2: C, 74.29; H, 6.03; N, 5.78. Found: C, 74.30; H, 6.05; N, 5.75.