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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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7 (459.45): C, 67.97; H, 4.61; N, 3.05. Found: C, 67.86; H, 4.73; N, 2.98.
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50
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62349139349
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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
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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 ftp://davinci.chem.umanitoba.ca.
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51
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