Diastereo- and regioisomeric bicyclic thiohydantoins from chiral 1,3- thiazolidine-2,4-dicarboxylic acids

I. Miskolczi, A. Zekany, F. Rantal, A. Linden, K. Kövér, Z. Györgydeák

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Bicyclic thiohydantoins were synthesized in a stereoselective manner by reacting (2R)/(2S)-diastereoisomer mixtures of 1,3-thiazolidine-2,4- dicarboxylic acids or their dimethyl diesters with PhNCS. 5,5-Dimethyl-1,3- thiazolidine-2,4-dicarboxylic acid with PhNCS led to a cyclization involving the C=O group at the C(2) center of the thiazolidine ring, while the acid's dimethyl diester gave cyclization involving the C=O group at C(4). In contrast, reactions involving unsubstituted 1,3-thiazolidine-2,4-dicarboxylic acid or its dimethyl diester led to thiohydantoins in which the ring closure had taken place only with the COO group at C(4). Independently of the direction of the ring closure, all reactions produce exclusively products with the (R)-configuration at C(2). The configurational assignments were based on 1H- and 13C-NMR studies, and confirmed by X-ray crystallographic analyses.

Original languageEnglish
Pages (from-to)744-753
Number of pages10
JournalHelvetica Chimica Acta
Volume81
Issue number4
Publication statusPublished - 1998

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Thiohydantoins
dicarboxylic acids
Cyclization
closures
Acids
rings
Thiazolidines
Nuclear magnetic resonance
X-Rays
X rays
nuclear magnetic resonance
acids
products
configurations
2-carboxythiazolidine-4-carboxylic acid
x rays

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Diastereo- and regioisomeric bicyclic thiohydantoins from chiral 1,3- thiazolidine-2,4-dicarboxylic acids. / Miskolczi, I.; Zekany, A.; Rantal, F.; Linden, A.; Kövér, K.; Györgydeák, Z.

In: Helvetica Chimica Acta, Vol. 81, No. 4, 1998, p. 744-753.

Research output: Contribution to journalArticle

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AU - Miskolczi, I.

AU - Zekany, A.

AU - Rantal, F.

AU - Linden, A.

AU - Kövér, K.

AU - Györgydeák, Z.

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N2 - Bicyclic thiohydantoins were synthesized in a stereoselective manner by reacting (2R)/(2S)-diastereoisomer mixtures of 1,3-thiazolidine-2,4- dicarboxylic acids or their dimethyl diesters with PhNCS. 5,5-Dimethyl-1,3- thiazolidine-2,4-dicarboxylic acid with PhNCS led to a cyclization involving the C=O group at the C(2) center of the thiazolidine ring, while the acid's dimethyl diester gave cyclization involving the C=O group at C(4). In contrast, reactions involving unsubstituted 1,3-thiazolidine-2,4-dicarboxylic acid or its dimethyl diester led to thiohydantoins in which the ring closure had taken place only with the COO group at C(4). Independently of the direction of the ring closure, all reactions produce exclusively products with the (R)-configuration at C(2). The configurational assignments were based on 1H- and 13C-NMR studies, and confirmed by X-ray crystallographic analyses.

AB - Bicyclic thiohydantoins were synthesized in a stereoselective manner by reacting (2R)/(2S)-diastereoisomer mixtures of 1,3-thiazolidine-2,4- dicarboxylic acids or their dimethyl diesters with PhNCS. 5,5-Dimethyl-1,3- thiazolidine-2,4-dicarboxylic acid with PhNCS led to a cyclization involving the C=O group at the C(2) center of the thiazolidine ring, while the acid's dimethyl diester gave cyclization involving the C=O group at C(4). In contrast, reactions involving unsubstituted 1,3-thiazolidine-2,4-dicarboxylic acid or its dimethyl diester led to thiohydantoins in which the ring closure had taken place only with the COO group at C(4). Independently of the direction of the ring closure, all reactions produce exclusively products with the (R)-configuration at C(2). The configurational assignments were based on 1H- and 13C-NMR studies, and confirmed by X-ray crystallographic analyses.

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