Novel Syntheses of alpha,beta-Unsaturated Esters, alpha,beta-Unsaturated gamma-Lactones, and 2-Alkoxypyrroles via 1,2,4-Triazole-Stabilized Allenic Anions.
J Org Chem
; 62(3): 715-720, 1997 Feb 07.
Article
em En
| MEDLINE
| ID: mdl-11671469
ABSTRACT
The dianion 12 (right harpoon over left harpoon 13) of 1-(1,2,4-triazol-1-yl)phenylpropargyl ethyl ether 11(readily prepared from phenylpropargylaldehyde diethyl acetal 8 and 1,2,4-triazole) reacts with alkyl halides, aldehydes, ketones, and alpha,beta-unsaturated ketones to give exclusively gamma-substituted allenic products of type 10. These adducts underwent mild in situ hydrolysis enabling convenient syntheses of alpha,beta-unsaturated esters 9a-c and alpha,beta-unsaturated gamma-lactones 16, 18, 20, and 22. Reactions of dianion 13 with imines generated the 1,3,4-trisubstituted 2-alkoxypyrroles 27, 30, and 31 in high yields. The alkyl-substituted analog 34 underwent similar reactions to give predominantly the gamma-products 39,40, and 42 along with a small proportion of alpha-analogs.
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01-internacional
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MEDLINE
Idioma:
En
Ano de publicação:
1997
Tipo de documento:
Article