- 3-Hydroxypyrroles and 1H-Pyrrol-3(2H)-ones. Part 10. Alkylation of Pyrrolones under Basic Conditions: Regiospecific Formation of 3-Alkoxypyrroles
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Alkylation of 1-substituted 1H-pyrrol-3(2H)-ones 1 in the presence of base generally gives a mixture of O-alkylated 3, C,O-dialkylated 4 and C,C-dialkylated 5 products.The proportion of C-alkylation is increased by the use of a soft alkylating agent (e.g. iodomethane) and a solvent of l ow polarity (e.g.THF), whereas O-alkylation is favoured by hard alkylating agents (e.g. methyl toluene-p-sulphonate), and dipolar aprotic solvents (e.g. dimethylimidazolidinone).These latter conditions give a good preparative route to a wide range of 1-substituted and 1,2-disubstituted 3-alkoxypyrroles 3 (65-90percent yield).The X-ray crystal structure of 1-tert-butyl-3-methoxy-2-phenylpyrrole 22 is reported.
- Hunter, Gordon A.,McNab, Hamish,Monahan, Lilian C.,Blake, Alexander J.
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p. 3245 - 3251
(2007/10/02)
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- 3-Hydroxypyrroles and 1H-Pyrrol-3(2H)-ones. Part 1. Formation and X-Ray Crystal and Molecular Structure of 1-cyclohexyl-2,2-pentamethylene-1H-pyrrol-3(2H)-one
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The title compound (4) is formed by flash vacuum pyrolysis of a dicyclohexylaminomethylene derivative of Meldrum's acid, (2) and its structure was determined by X-ray crystallograhy.Deuterium-labelling studies show that the reaction mechanism involves a s
- Hickson, Clare L.,Keith, Eileen M.,Martin, Jane C.,McNab, Hamish,Monahan, Lilian C.,Walkinshaw, Malcolm D.
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p. 1465 - 1470
(2007/10/02)
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- 3-Hydroxypyrroles
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Simple 3-hydroxypyrroles are obtained by pyrolysis of appropriate aminomethylene Meldrum's acid derivatives: the unusual reactions of these compounds with acids, bases, and electrophiles is discussed.
- McNab, Hamish,Monahan, Lilian C.
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p. 213 - 214
(2007/10/02)
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