- Synthesis and nucleophilic properties of 1,2 -dialkyl-3-nitropyrroles and 1,5-dialkyl-4-nitropyrrole-2-carboxylic acid derivatives
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1,2-Dialkyl-3-nitropyrroles 1 are versatile synthetic tools for obtaining substituted pyrrolidines or fused ring heterocycles such as pyrrolopyridines, pyrrolopyrimidines or pyrroloazepines. We have established a method for obtaining compounds related to structure 1 and studied the reactivity as a nucleophile of the benzylic type moiety in the alkyl residue bound to position 2.
- Molins-Pujol, Antoni M.,Moranta, Concepcio,Arroyo, Carmina,Rodriguez, M. Teresa,Meca, M. Carmen,Pujol, M. Dolors,Bonal, Joaquim
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p. 2277 - 2289
(2007/10/03)
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- 1-AZABICYCLIC COMPOUNDS. 24. SELECTIVITY OF POSITION OF NITRATION OF 1,2-DIHYDROPYRROLIZINE, 5,6,7,8-TETRAHYDROPYRROCOLINE AND PYRROLE HOMOLOGS
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The selectivity of the position of nitration of 1-methylpyrrole, 1,2-dimethylpyrrole, 1,2-dihydropyrrolizine, and 5,6,7,8-tetrahydropyrrocoline was found.In contrast to the selectivity of substitution during nitration of their carbocyclic analogs, o-xylene, indane, and tetraline, the fraction of the α-nitro-isomer in the nitration products of 1,2-dimethylpyrrole is smaller than the fraction of α-nitro derivatives of 1,2-dihydropyrrolizine and 5,6,7,8-tetrahydropyrrocoline, and in the latter cases the isomers are almost equally distributed.During nitration of the above bicyclic pyrroles, the Mills-Nixon effect does not appreciably influence the selectivity of the position of the reaction.
- Skvortsov, I. M.,Astakhova, L. N.
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p. 1189 - 1191
(2007/10/02)
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- PREPARATIVE ASPECTS OF THE NITRATION OF 1-METHYLPYRROLE DERIVATIVES. 13C NMR OF SOME NITROPYRROLES.
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The nitration of 1-methylpyrrole and 1,2-dimethylpyrrole was studied and the products were characterized. It was found that the nitration of ethyl 1-methylpyrrole-2-carboxylate depends on the reaction conditions. **1**3C parameters have been determined for several 1-methyl substituted pyrrole- and nitropyrrole derivatives and the relationship between the observed and predicted **1**3C shifts for aromatic carbons is briefly discussed. It has been found that the determination of the direct **1**3C-**1H coupling constants in the pyrrole ring constitutes a useful tool for distinguishing alpha - and beta -positions.
- Grehn
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