Reaction of Pteridine and Its 8-0xide with Grignard Reagents, Regioselective 7-Alkylation of Pteridine
Reaction of 2-amino-4-butoxypteridine (1) with alkyl- or phenylmagnesium bromide followed by protonative and oxidative work-up with a solution of iodine in acetic acid gives 7 -alkyl- or 7 -phenylpteridines (2 ). Regioselective oxidation of 1 to 2-amino-4-butoxypteridine 8-oxide (3) by hydrogen pero...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
| Published: |
De Gruyter
1995-11-01
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| Series: | Pteridines |
| Subjects: | |
| Online Access: | https://doi.org/10.1515/pteridines.1995.6.4.160 |
| Summary: | Reaction of 2-amino-4-butoxypteridine (1) with alkyl- or phenylmagnesium bromide followed by protonative and oxidative work-up with a solution of iodine in acetic acid gives 7 -alkyl- or 7 -phenylpteridines (2 ). Regioselective oxidation of 1 to 2-amino-4-butoxypteridine 8-oxide (3) by hydrogen peroxide proceeds in trifluoroacetic acid, and reaction of 3 with Grignard reagent or an organolithium compound affords 2 together with its 8-oxide 4. The products (2 and 4) are easily derived to 7-substituted 2-amino-4- hydroxypteridines. The mechanism of the regioselectivity can be explained based on electron density and molecular orbitals (MO) which are obtained by calculation on the methoxy analogs of 1 and 3. |
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| ISSN: | 0933-4807 2195-4720 |