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| Title: | Cycloaddition Reactions: Reaction of 3-Methyl-2-phenylpyrrocoline with Dimethyl Acteylenedicarboxylate |
| Authors: | Gupta, C M
Rizvi, R K
Anand, Nitya
Murthy, M R Narsimha
Venkatesan, K |
| Issue Date: | 1981 |
| Citation: | lndian Journal of Chemistry (1981), 20B, 735-741 |
| Series/Report no.: | CDRI Communication Number 2980 |
| Abstract: | Reaction of 3-methyl-2-phenylpyrrocoline(I) and dimethyl acetylenedicarboxylate(II) in refluxing toluene furnishes cis-7',8-dihydro.4,5,8,9-tetramethoxycarbonyl-7'-phenyl-7' -methylazocino(2,1,8-cd]pyrrolizine (III) and trans-7',8-dihydro-4,5,8,9-tetramethoxycarbonyl-7-phenyl-7'-methylazocino[2,1,8-cd]pyrrolizine (IV), while the same reaction at ambient temperature yields 1-[(1,2-trans-dimethoxycarbonyl)vinyl]-3-methyl-2-phenylpyrrocoline (V) and 1-[(1,2-cis-di(methoxycarbonyl)vinyl)--methyl-2- phenylpyirocoUne (V) and
1-[(I,2-cis-di(methoxycarbonyl)Yinyl]-3-metbyl-2-phenylpyrrocoline(VI) as the major products. The structure of IV
has been determined by X-ray crystallography.A possible mechanism of formation of these products is also discussed. |
| URI: | http://hdl.handle.net/123456789/118 |
| Appears in Collections: | Medicinal and Process Chemistry
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