Construction of 6-Amino-2,2-Dimethyl-3,4,6-Trisubstituted-2H-1-Benzopyran Library by Solid Phase Synthesis

Gong, Y.; Seo, J.; Chon, Y.; Hwang, J.; Park, J.; Yoo, S. Construction of 6-Amino-2,2-Dimethyl-3,4,6-Trisubstituted-2H-1-Benzopyran Library by Solid Phase Synthesis. J. Comb. Chem. 2003, 5, 577-589.

We report the solid-phase library construction of 2000 analogues of 6-amino-2,2-dimethyl-3,4,6-trisubstituted-2H-1-benzopyran. The polymer-bound hydroxyalkoxychromanes 5, produced by nucleophilic reactions with various alcohols on epoxides generated in situ, served as key intermediates for subsequent diversification.  Further reactions on these hydroxyalkoxychromanes 5 with various electrophiles, such as alkyl halides and acid halides, produced the desired 6-amino-2,2-dimethyl-3,4,6-trisubstituted-2H-1-benzopyran analogues 9, 10, and 11. The progress of reactions could be monitored as solid-bound intermediates by ATR-FTIR or HR-MAS-NMR spectroscopy. The final compounds, obtained in good yields and high purity upon cleavage from the resins, were characterized by LC/MS, HRMS, 1H NMR, and 13C NMR spectroscopy.

Construction of 6-Amino-2,2-Dimethyl-3,4,6-Trisubstituted-2H-1-Benzopyran Library by Solid Phase Synthesis

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