STUDIES ON CONJUGATED NITRILES .7. LEWIS ACID-PROMOTED REACTION OF ACTIVE METHYLENE-COMPOUNDS WITH DIETHYL PHOSPHOROCYANIDATE - PREPARATION OF ALPHA,BETA-UNSATURATED ALPHA-AMINOPHOSPHONATES
Sakamoto, M; Fukuda, Y; Kamiyama, T; Kawasaki, T
| HERO ID | 4935910 |
|---|---|
| In Press | No |
| Year | 1994 |
| Title | STUDIES ON CONJUGATED NITRILES .7. LEWIS ACID-PROMOTED REACTION OF ACTIVE METHYLENE-COMPOUNDS WITH DIETHYL PHOSPHOROCYANIDATE - PREPARATION OF ALPHA,BETA-UNSATURATED ALPHA-AMINOPHOSPHONATES |
| Authors | Sakamoto, M; Fukuda, Y; Kamiyama, T; Kawasaki, T |
| Journal | Chemical and Pharmaceutical Bulletin |
| Volume | 42 |
| Issue | 9 |
| Page Numbers | 1919-1921 |
| Abstract | Reaction of diethyl phosphorocyanidate (DEPC) with dimethyl malonate (1a) and ethyl cyanoacetate (1b) in the presence of zinc chloride and triethylamine resulted in selective addition of 1a,b to the cyano group of DEPC to give alpha,beta-unsaturated alpha-aminophosphonates (2a,b). In contrast, similar treatment of enolizable methyl acetoacetate (1c) and acetylacetone (1d) with DEPC gave the corresponding enolphosphates (4c,d) as a result of nucleophilic displacement on the phosphorus atom of DEPC. Conversion of the resulting alpha-aminophosphonate (2a) to uracil-6-phosphonates (6a,b) was achieved by treatment with phenyl isocyanate (5a) and isothiocyanate (5b), respectively. |
| Wosid | WOS:A1994PH63400039 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | DIETHYL PHOSPHOROCYANIDATE; ZINC CHLORIDE; ALPHA-AMINOPHOSPHONATE; URACIL-6-PHOSPHONATE; ENOLPHOSPHATE |
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