Fischer Indolization and Its Related Compounds. VIII. Formation of 4-Aminoindole Derivatives on the Fischer Indolization of 2-Methoxyphenylhydrazone Derivatives
Ishii, H; Murakami, Y; Takeda, H; Furuse, T
| HERO ID | 4933265 |
|---|---|
| In Press | No |
| Year | 1974 |
| Title | Fischer Indolization and Its Related Compounds. VIII. Formation of 4-Aminoindole Derivatives on the Fischer Indolization of 2-Methoxyphenylhydrazone Derivatives |
| Authors | Ishii, H; Murakami, Y; Takeda, H; Furuse, T |
| Journal | Chemical and Pharmaceutical Bulletin |
| Volume | 22 |
| Issue | 9 (1974) |
| Page Numbers | 1981 |
| Abstract | Fischer indolization of ethyl pyruvate 5-chloro-2-methoxyphenylhydrazone (6) with anhydrous zinc chloride gave ethyl 4-amino-6-chloroindole-2-carboxylate (12) as a main product, with three other expected in doles, (7), (8) and (5). Cyclization of ethyl pyruvate 2-methoxyphenylhydrazone (1) with p-toluenesulfonic acid in the presence of diethyl malonate afforded ethyl 4-(ethoxycarbonylacetamido)-indole-2-carboxylate (28) and diethyl 4-(ethoxycarbonylacetamido)-3, 6'-biindole-2, 2'-dicarboxylate (30) with five other indole derivatives, (11), (10), (26), (27), and (32). The pathway leading to such a 4-aminoindole product in the abnormal Fischer indolization of a 2-methoxyphenylhydrazone derivative is discussed. |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |