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We found that heating the propenoate 13p in CF3COOH gives the pyrrole 91a in 65% yield

Synthesis of heterocycles from alkyl 3-(dimethylamino)propenoates and related enaminones.

CHEMICAL REVIEWS, no. 5.0 (2004): 2433-2480

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简介
  • Branko Stanovnik was born in Slovenia in 1938
  • He received his diploma in chemistry in 1960 and his Ph.D. in organic chemistry at the University of Ljubljana in 1964.
  • Jurij Svete was born in Ljubljana, Slovenia, in 1962
  • He received his diploma in chemistry in 1986 and his Ph.D. in 1990 under the supervision of Professor Stanovnik.
  • They used propenoate 3 as the reagent for the preparation of N-benzoyl-R, -dehydrotryptophane ester 4 by dimethylamine substitution with indole.
  • Preparation of Alkyl 3-(Dimethylamino)propenoates and Analogues by Condensation between Substituted Acetic Acid Ester and Amide Acetal (Method A)
重点内容
  • Branko Stanovnik was born in Slovenia in 1938
  • His research interests lie in the synthesis and transformations of heterocyclic chemistry, asymmetric synthesis, and natural products derived from amino acids
  • His research interests include the synthesis of heterocyclic compounds with emphasis on chiral functionalized heterocycles containing an amino acid, peptide, amino alcohol, polyol, and related structural motifs
  • In this review we demonstrate how a series of 2-substituted 3-(dimethylamino)propenoates and related enaminones as masked R-formyl-R-substituted acid derivatives and ketones, including chiral analogues, has been developed into a group of versatile reagents for the preparation of 2,3-disubstituted propenoates and numerous monocyclic and fused heterocyclic systems with an R-amino acid or other related structural element incorporated into the newly formed heterocyclic system
  • Most of these reagents are accessible from or commercially available starting materials. Their applicability has been extended to the preparation of some natural products and their analogues, 3-heteroarylalanines, alaninols, lactic acid esters, diols, and heterocyclic compounds with incorporated dipeptide structural element
结果
  • 3-amino-4Hpyrido[1,2-a]pyrimidin-4-ones have been recently studied as fluorescent probes for hypoxic cells in solid tumors.[173].
  • They have been prepared, either in three steps by condensation of substituted 2-aminopyridines with ethyl 3-ethoxy-2-nitropropenoate followed by cyclization in polyphosphoric acid and reduction of the nitro group[174] or by hydrolysis of 3-benzoylamino-4H-pyrido[1,2-a]pyrimidin-4-ones in concentrated hydrochloric acid in yields below 30%.175
结论
  • In this review the authors demonstrate how a series of 2-substituted 3-(dimethylamino)propenoates and related enaminones as masked R-formyl-R-substituted acid derivatives and ketones, including chiral analogues, has been developed into a group of versatile reagents for the preparation of 2,3-disubstituted propenoates and numerous monocyclic and fused heterocyclic systems with an R-amino acid or other related structural element incorporated into the newly formed heterocyclic system.
  • The broad synthetic methodology and elaborated experimental techniques allow their application in the preparation of small libraries of these types of compounds by combinatorial approach
表格
  • Table1: Examples of 2-Alkyl-, 2-Aryl-, 2-Heteroaryl-, and 2-Acyl-3-(dimethylamino)propenoates 14
  • Table2: Table 2
  • Table3: Alkyl 2-(Vinylamino)-3-(dimethylamino)propenoates 13 compd R1 amide
  • Table4: Table 4
  • Table5: Heterocyclic Analogues of 2-Substituted 3-(Dimethylamino)propenoates 2 and 16-23
  • Table6: Chiral Cyclic Analogues of 2-Substituted 3-(Dimethylamino)propenoates 24-28 compd type
  • Table7: Table 7
  • Table8: Table 8
  • Table9: X-ray Structures of 2-Substituted Alkyl 3-(Dimethylamino)propenoates and Their Analogues. Continued)
  • Table10: NMR Structural Studies on 2-Substituted Alkyl 3-(Dimethylamino)alk-2-enoates and Their Analogues
  • Table11: NMR Structural Studies on Isomerization of 2-Substituted Alkyl 3-(Dimethylamino)propenoates and Their Analogues in Solution
  • Table12: Enehydrazine-Hydrazone Isomerization of 3-(Hydrazino)propenoates 63, 64
  • Table13: Alkyl 3-Acyloxy-2-[(2,2-disubstitutedethenyl)amino]propenoates 69a-j Prepared[<a class="ref-link" id="c80" href="#r80">80</a>] compd
  • Table14: Some Examples of -Aminodehydroalanine
  • Table15: Table 15
  • Table16: Dialkyl 3-Aminopyrrole-2,4-dicarboxylates 88a-h Prepared[<a class="ref-link" id="c42" href="#r42">42</a>] methcompd od
  • Table17: Alkyl 2-Pyrrolecarboxylates 91a-h Prepared methcompd od
  • Table18: Isoxazole-4-carboxylates 100a-k Prepared from Alkyl 2-Acyl-3-(dimethylamino)propenoates 14g-l,n,q,s-u107 yield
  • Table19: Pyrazole-4-carboxylates 111a-q from
  • Table20: Pyrazoles 117 and 120 Prepared from 4-(Dimethylamino)ethylidene-5(4H)-oxazolone 2k35,55 yield (%)
  • Table21: Hydrazinoazines 134a-g, Enehydrazines 135a-g, Hydrazones 136a-g, and Fused 1,2,4-Triazoles 137a-g62
  • Table22: Fused 2H-Pyran-2-ones 140-146 Prepared from 3-(Dimethylamino)propenoates 3, 13-15, and Carbocyclic and Heterocyclic Analogues of 1,3-Dicarbonyl Compoundsa compd R2 R3 X Y
  • Table23: Dialkyl 1-Substituted 1,4-Dihydro-4-oxopyridine-3,5-dicarboxylates 147a-t64 yield
  • Table24: Table 24
  • Table25: Table 25
  • Table26: Fused Pyrimidones 165-172 Prepared (Table of Substituents)a compd
  • Table27: Aplysinopsin Analogues 42 and 43 Prepared According to Methods A and B
  • Table28: Pyrimidinetrione Analogues of Aplysinopsins 184a-i
  • Table29: S)-N-Acyl-3-(1-substituted-5-hydroxy1H-pyrazol-4-yl)alanine Methyl Esters 197a-j156 compd
  • Table30: S)-N-Benzoyl-3-(4-oxo-4H-quinolizin-3-yl)- (198a-d) and (S)-N-Benzoyl-3-(2-oxo-2H-pyran-3-yl)alanine Methyl Esters (199a-i)[<a class="ref-link" id="c155" href="#r155">155</a>]
  • Table31: O-Benzoyl-2-(benzoylamino)-3-heteroaryl-1-propanols 200a-c and 201a-f59
  • Table32: Methyl (S)-3-(4-Oxo-4H-quinolizin-3-yl)- (202a-c), (S)-3-(2-Oxo-2H-pyran-3-yl)- (203a-j), and (S)-3-(4-Oxo-4H-pyridino[1,2-a]pyrimidin-3-yl)lactates (204a,b)[<a class="ref-link" id="c84" href="#r84">84</a>,<a class="ref-link" id="c168" href="#r168">168</a>]
  • Table33: Table 33
  • Table34: Stereoselective Amination of 5-Substituted γ-Lactones and γ-Lactams[<a class="ref-link" id="c57" href="#r57">57</a>] compd
  • Table35: Dipeptide Analogues 212-214 and 216-218 of Type B
  • Table36: Pyrrolo[3,4-c]pyrazoles 221a-d and Pyrrolo[4,3-d]isoxazoles 222a,b Prepared[<a class="ref-link" id="c58" href="#r58">58</a>,<a class="ref-link" id="c68" href="#r68">68</a>] compd R
  • Table37: Table 37
  • Table38: N-Heteroarylhydrazones 228-230 Prepared from Heteroaryldiazonium Tetrafluoroborates and 1,3-Dicarbonyl Compounds[<a class="ref-link" id="c180" href="#r180">180</a>]
  • Table39: Table 39
  • Table40: Experimental Data for Reactions of Diazonium Salts 226a,b with Alcohols[<a class="ref-link" id="c179" href="#r179">179</a>] reaction
  • Table41: Table 41
  • Table42: Methyl 2-(Acetylamino)-3-arylaminopropenoates 252186 and r-Arylaminomethylidene- benzyloxycarbonyl-amino-γ-butyrolactones 25361 Prepared by Parallel Solution Phase Approach a Reaction conditions: (i) MeNH2, H2O, 150 °C; (ii) DMFDEA, 4-phenoxyacetophenone, DMF, 150 °C; (iii) DMFDEA, ethyl (4-nitrobenzoyl)acetate, DMF, 150 °C; (iv) NH2OH × HCl, EtOH, 180 °C; (v) PhNHNH2, AcOH, or EtOH, 180 °C; (vi) benzamidine hydrochloride, KOH, DMF, 180 °C. All reactions were carried out under microwave irradiation
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基金
  • For example, 3-amino-4Hpyrido[1,2-a]pyrimidin-4-ones have been recently studied as fluorescent probes for hypoxic cells in solid tumors.[173]. They have been prepared, either in three steps by condensation of substituted 2-aminopyridines with ethyl 3-ethoxy-2-nitropropenoate followed by cyclization in polyphosphoric acid and reduction of the nitro group[174] or by hydrolysis of 3-benzoylamino-4H-pyrido[1,2-a]pyrimidin-4-ones in concentrated hydrochloric acid in yields below 30%.175
研究对象与分析
papers: 500
He was a postdoctorate fellow with the National Research Council in Canada and a Visiting Professor in the United States and Australia. He is a member of many advisory boards and societies and the author of over 500 papers, reviews, and books. His research interests lie in the synthesis and transformations of heterocyclic chemistry, asymmetric synthesis, and natural products derived from amino acids

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