| Autor: |
Wade PA; Department of Chemistry, Drexel University, Philadelphia, Pennsylvania 19104, USA., Le H, Amin NV |
| Jazyk: |
angličtina |
| Zdroj: |
The Journal of organic chemistry [J Org Chem] 2002 May 03; Vol. 67 (9), pp. 2859-63. |
| DOI: |
10.1021/jo010924k |
| Abstrakt: |
Racemic N-methyl-S-(nitromethyl)-S-phenylsulfoximine (2) was prepared in 87% yield via alkaline nitration of N,S-dimethyl-S-phenylsulfoximine. Optically active N-methyl-S-(nitromethyl)-S-phenylsulfoximine (both enantiomers) was prepared in similar fashion. Reaction of racemic 2 with p-chlorophenyl isocyanate and a catalytic quantity of triethylamine in the presence of furan afforded dihydrofuroisoxazole 5, the product of nitrile oxide cycloaddition, in 42% yield (65:35 diastereomer ratio). Reaction of the dihydrofuroisoxazole 5 with phenyllithium and methyllithium afforded replacement of the sulfoximine group by phenyl and methyl, respectively. Reaction of racemic 2 with aromatic isocyanates and potassium carbonate afforded C-acylation products in 70-78% yield which existed as the ylide tautomers 9a,b. Methylation of racemic 2 afforded the C-alkylate N-methyl-S-(1-nitroethyl)-S-phenylsulfoximine (13), existing as the neutral tautomer. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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