Abstract
Alkoxycarbonylation of dihydropyrimidin-2-one 1 with alkyl chloroformate in the presence of NaH occurred regioselectively at position-3 to provide N-substituted dihydropyrimidin-2(1H)-one 2, but the reaction of 1 with trichloromethyl chloroformate (phosgene dimer) and aminoalcohol in the presence of NaH and Et3N afforded regioselectively N-substituted dihydropyrimidin-2(3H)-one 3 or compound 2. In this case, regioselectivity was dependent upon the substitution pattern of the phenyl ring. The reaction of 1 with phosgene dimer and ordinary alcohol in the base gave regioselectively compound 3 in contrast to the result of alkyl chloroformate method.
Original language | English |
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Pages (from-to) | 5405-5408 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 29 |
Issue number | 42 |
DOIs | |
Publication status | Published - 1988 |
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry