C-Functionalization of 9-deazapurines by cross-coupling reactions |
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Authors: | Vítězslav Bambuch Radek Pohl Milena Masojídková Antonín Holý |
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Institution: | Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic |
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Abstract: | C-Functionalization of pyrrolo3,2-d]pyrimidine scaffold in positions 2, 4, and 7 using cross-coupling reactions was performed. Thus, 2-(5-(benzyloxymethyl)-2,4-dichloro-5H-pyrrolo3,2-d]pyrimidin-7-yl)ethanol, a versatile synthetic precursor for 9-deazapurines and 4,6-diazaindoles, was prepared by vinylation of the corresponding iodide followed by hydroboration of the double bond. A synthesis of 9-(1,2-dihydroxyethyl)-9-deazaadenine, a 9-deaza-1′-nor congener to antiviral DHPA, was developed. In addition, an abnormal regioselectivity in methylalumination of the terminal triple bond in position 7 of the pyrrolo3,2-d]pyrimidine scaffold leading to a transformation into (Z)-prop-1-enyl was observed. |
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Keywords: | Nucleobase Nucleoside 9-Deazaadenine Carbometalation Carboalumination |
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