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Construction of 6-amino-2,2-dimethyl-3,4,6-trisubstituted-2H-1-benzopyran Library by Solid Phase Synthesis

Construction of 6-amino-2,2-dimethyl-3,4,6-trisubstituted-2H-1-benzopyran Library by Solid Phase Synthesis

Young-Dae Gong, Jin-Soo Seo, Yong Sog Chon, Jong Yeon Hwang, Ji Yeon Park, Sung-Eun Yoo

J Comb Chem. Sep-Oct 2003;5(5):577-89.

PMID: 12959558

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP864079629	2,2-Dimethyl-3,6,9,12-tetraoxa-2-silatridecane		864079-62-9	Price

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