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Volumn , Issue 2, 2009, Pages 229-232

Methylisoquinoline-based three-component condensation reactions involving chromone-3-carboxaldehydes: One-pot synthesis of a new class of chromenopyridoisoquinolines

Author keywords

Acetylenedicarboxylate; Chromenopyridoisoquinolines; Chromone 3 carboxaldehydes; Isoquinoline; Multicomponent reactions

Indexed keywords


EID: 62349134360     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087517     Document Type: Article
Times cited : (14)

References (51)
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    • All melting points were determined on a Büchi apparatus and are uncorrected. The 1H NMR and 13C NMR spectra were recorded on a Bruker AM300 spectrometer in CDCl3 with TMS as internal standard. All coupling constants are given in Hz and chemical shifts are given in ppm. Typical Experimental Procedure for the Preparation of 3a: DMAD (1.0 mmol) was added to a stirred solution of chromone-3-carboxaldehyde 1a (1.0 mmol) and isoquinoline (1.0 mmol) in DME (20 mL) at r.t. and the reaction mixture was stirred for 12 h. Distillation of the solvent in vacuo followed by column chromatography using petroleum ether-EtOAc (3:1) as eluent afforded the chromenopyridoisoquinoline 3a (Scheme 1, Yield: 54, yellow crystals; mp 206-207°C (EtOH, IR (KBr, 1728, 1704, 1665, 1607 cm -1. 1H NMR (300 MHz, CDCl3, δ, 1.82 (d, J, 0.8 Hz, 3 H, 6-Me, 3.85 (s, 3 H, 8-COOMe, 3.90 s, 3 H, 9-COOMe, 5.14
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    • The multiplicities and chemical shifts of the aromatic protons have been confirmed after simulation with program SpinWorks, version 2.2.0, available from
    • The multiplicities and chemical shifts of the aromatic protons have been confirmed after simulation with program SpinWorks, version 2.2.0, available from ftp://davinci.chem.umanitoba.ca.
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