Conversion of 4-Oxoproline Esters to 4-Substituted Pyrrole-2-carboxylic Acid Esters

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Conversion of 4-oxoproline esters to 4-substituted pyrrole-2-carboxylic acid esters.

The Grignard, Wittig, Tebbe, Horner-Emmons, and Reformatsky reactions of the 4-oxoproline esters gave the corresponding 4-alylated or 4-alkylidenated products, respectively. The products were properly treated with bases to cause aromatization, giving 4-substituted pyrrole-2-carboxylic acid esters such as methyl 4-methylpyrrole-2-carboxylate, which is a trail pheromone of Atta texana.

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Synthesis of Pyrrole Phosphonate Esters: Emphasis on Pyrrole NH Acids and Dialkylacetylenic Esters Substitution

Reaction of dialkyl acetylenedicarboxylates 1a-c andpyrrole derivatives 2a-e in the presence of triphenylphosphite (TPP) was investigated and the effect of the pyrrole substitution was established. Diastereoselectivity is observed with pyrroles, 2a,b, yieldingphosphonate ester derivatives 3a-f and 4,and their relative configuration is determined by 1H/13C and 31</...

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Esters and Related Carboxylic Acid Derivatives

The ester functionality does not introduce a center of asymmetry and thus optical and geometric isomerism does not result from the presence of this functional group. The ester functionality (the carbonyl and ether oxygen) is composed of an sp hybridized carbon so it cannot be chiral, and since there is free rotation about the ether bond geometric isomerism also is not possible at the sp center....

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1H-Pyrrole-2-carboxylic acid

In the title compound, C(5)H(5)NO(2), the pyrrole ring and its carboxyl substituent are close to coplanar, with a dihedral angle of 11.7 (3)° between the planes. In the crystal structure, adjacent mol-ecules are linked by pairs of O-H⋯O hydrogen bonds to form inversion dimers. Additional N-H⋯O hydrogen bonds link these dimers into chains extending along the a axis.

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ژورنال

عنوان ژورنال: Chemical and Pharmaceutical Bulletin

سال: 2009

ISSN: 0009-2363,1347-5223

DOI: 10.1248/cpb.57.167