Construction of 6-amino-2,2-dimethyl-3,4,6-trisubstituted-2H-1-benzopyran library by solid phase synthesis.
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, (1)H NMR, and (13)C NMR spectroscopy.
Gong
Young-Dae
YD
Medicinal Science Division, Korea Research Institute of Chemical Technology, P.O. Box 107, Yusung, Taejon 305-600, Korea.
Seo
Jin-Soo
JS
Chon
Yong Sog
YS
Hwang
Jong Yeon
JY
Park
Ji Yeon
JY
Yoo
Sung-Eun
SE
D001578:Benzopyrans / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry*; D013678:Technology, Pharmaceutical / Q000379:methods*
D001578:Benzopyrans