Alkyl 2-Substituted 3-(Dimethylamino)propenoates and Related Compounds - Versatile Reagents in Heterocyclic Chemistry

doi:10.1055/s-2000-6732

Synlett

2000

DOI: 10.1055/s-2000-6732

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Alkyl 2-Substituted 3-(Dimethylamino)propenoates and Related Compounds - Versatile Reagents in Heterocyclic Chemistry

Abstract: Alkyl 2-substituted 3-(dimethylamino)propenoates and related compounds, masked a-formyl-a-amino-and a-formyl-a-hydroxy acid derivatives, available in one step from 2-substituted acetic acid derivatives by treatment with amide acetals, represent a useful synthetic tool for a simple preparation of various heterocyclic systems and aryl-and heteroaryl substituted amino acid derivatives. On the other hand, 3-(dimethylamino)propenoates can also serve as reagents for the protection of amino group, e. g. in peptide sy… Show more

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Cited by 17 publications

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Synthesis of Enediamino Amino Acid Analogues and Peptides

et al. 2017

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Enediamino peptides and their constituent element enediamino aminoa cids are rich resources for the developmento fb oth biologically potent compounds and valuable synthetic intermediates. However,d espite tireless efforts, the synthesis of the unique enediamino functionality is still elusive, particularly in the case of enediamino peptides. This review providesacomprehensive account of the reported methods fort he syntheses of enediamino amino acid analoguesa nd peptides.

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Synthesis of Enediamino Amino Acid Analogues and Peptides

et al. 2017

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ChemInform Abstract: Alkyl 2‐Substituted 3‐(Dimethylamino)propenoates and Related Compounds — Versatile Reagents in Heterocyclic Chemistry

Stanovnik

Svete

2000

ChemInform

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The synthesis and transformations of 2‐[2‐ethoxycarbonyl‐2‐(2‐pyridinyl)ethenyl]amino‐3‐dimethylaminopropenoates. the synthesis of substituted β‐amino‐α,β‐didehydro‐a‐amino acid derivatives

Jukic

Rečnik

Svete

et al. 2001

Journal of Heterocyclic Chem

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Alkyl (Z)-2-[(E)-2-ethoxycarbonyl-2-(2-pyridinyl)ethenyl]amino-3-dimethylaminopropenoates 7 and 8 were prepared from ethyl 2-pyridinylacetate (1) in two steps. Substitution of the dimethylamino group with alkyl-, aryl-, or heteroarylamines afforded the corresponding β-alkyl-22-24, β-aryl-25-35, and β-herteroarylamino-α,β-didehydro-α-amino acid 36 and 37 derivatives, intermediates for further preparation of various heterocyclic systems. The orientation around both double bonds were determined by various nmr techniques. J. Heterocyclic Chem., 38, 859 (2001).Recently, substituted 2-acylamino-or 2-hydroxy-3-(dimethylamino)propenoates as masked α-formyl-αamino-or α-formyl-α-hydroxy acid derivatives, and 2-[(2,2-disubstituted ethenyl)amino]-3-(dimethylamino)propenoates and related compounds have been prepared in our laboratory and used as reagents for preparation of various heterocyclic systems, such as 2H-pyran-2-ones and fused pyran-2-ones, fused pyridinones, pyrimidinones [1-10], imidazole-4-carboxylates [11], alkyl 1-acyl-3,4-disubstituted pyrrole-2-carboxylates [12,13], dialkyl 3-aminopyrrole-2,4-dicarboxylates and 5H-pyrrolo[3,2-d]pyrimidine derivatives [14], and (Z)-aplysinopsin analogs in a simple and stereoselektive manner [15]. Alkyl 2-[2cyano-2-(2-pyridinyl)ethenyl]amino-3-dimethylaminopropenoates have been transformed into alkyl 2-[2-cyano-2-(2-pyridinyl)ethenyl]amino-3-[2-methoxycarbonyl-4-(2-pyridinyl)-1H-pyrrol-3-yl]aminopropenoates [16]. Chiral 3-(dimethylamino)propenoate analogs derived from L-glutamic and L-pyroglutamic acid have been used for the preparation of (S)-3-(heteroaryl)alanine and (S)-3-(heteroaryl)lactic acid derivatives, as well as for the preparation of heterocyclic systems with an α-amino acid structural element incorporated into the cyclic system [17][18][19][20][21][22][23].In continuation of our studies in this area, we report the synthesis of alkyl (Z)-2-[(E)-2-alkoxycarbonyl-2-(2pyridinyl)ethenyl]amino-3-dimethylaminopropenoates 7 and 8, and their further transformations with alkyl-, aryl-, and heteroarylamines into β-alkyl (aryl and heteroaryl)aminoα,β-didehydro-α-amino acid derivatives 22-37 as intermediates for preparation of various heterocyclic systems.Alkyl (E)-N-[2-ethoxycarbonyl-2-(2-pyridinyl)ethenyl)glycinates 5 and 6 were prepared by heating a mixture of ethyl 2-pyridinylacetate (1) and N,N-dimethylformamid dimethylacetal (DMFDMA) or (t-butyloxy)bis(dimethylamino)methane (Bredereck's reagent) at 85 °C for 1.5 hours in an argon atmosphere to give ethyl 3-(dimethylamino-2-(2-pyridinyl)propenoate (2) followed, without purification, by treatment with an alkyl glycinate hydrochloride 3, 4 in ethanol by heating at reflux temperature for 1.5 hours in 80-86% yield. They were transformed with (t-butyloxy)-859

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Alkyl 2-Substituted 3-(Dimethylamino)propenoates and Related Compounds - Versatile Reagents in Heterocyclic Chemistry

Cited by 17 publications

References 19 publications

Synthesis of Enediamino Amino Acid Analogues and Peptides

Synthesis of Enediamino Amino Acid Analogues and Peptides

ChemInform Abstract: Alkyl 2‐Substituted 3‐(Dimethylamino)propenoates and Related Compounds — Versatile Reagents in Heterocyclic Chemistry

The synthesis and transformations of 2‐[2‐ethoxycarbonyl‐2‐(2‐pyridinyl)ethenyl]amino‐3‐dimethylaminopropenoates. the synthesis of substituted β‐amino‐α,β‐didehydro‐a‐amino acid derivatives

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