Asymmetric 1,3-Dipolar Cycloaddition Reactions

Chem. Pharm. Bull.(オピニオン)

Recent developments in the chemistry of enaminones

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

Compounds, pharmaceuticals, kits and methods are provided for use with DPP-IV and other S9 proteases that comprise a compound comprising: 
wherein M is N or CR 4 ; Q 1 and Q 2 are each independently selected from the group consisting of CO, SO, SO 2 , and C═NR 9 ; and each L, X, R 1 , R 2 , and R 3 are as defined herein.

Dipeptidyl peptidase inhibitors

A Simple Synthesis of Dimethyl 2‐[(Z)‐3‐Amino‐1‐oxo‐1‐(substituted)but‐2‐en‐2‐yl]fumarates: Potential Intermediates in the Synthesis of Polysubstituted Five‐ and Six‐Membered Heterocycles.

Herein a simple one-pot metal-free synthesis of alkyl-, aryl-, heteroaryl- and alkoxycarbonyl substituted 1,3-bis(dimethylamino)benzene derivatives is described. The products were prepared from the corresponding methyl ketones or compounds with an α-methylene group in regard to the carbonyl group, using N,N-dimethylacetamide dimethyl acetal (DMADMA) as the reagent.

Reactions of Enaminones and Related Compounds with N,N‐Dimethylacetamide Dimethyl Acetal. A Simple One‐Pot Metal‐Free Synthesis of Polysubstituted Benzene Derivatives.

Publisher Summary This chapter illustrates the usefulness of dialkyl acetone-1,3-dicarboxylates and their (dimethylamino) methylidene derivatives as versatile building blocks in the construction of many five- and six-membered heterocyclic systems, and their fused analogs. It describes the synthesis of various hetrocyclic compounds using chemical reactions performed on dialkyl acetone-1,3-dicarboxylates and derivatives. The synthesized compounds include 1-substituted 4-ethoxycarbonyl-5-(ethoxycarbonylmethyl)pyrazoles; pyrazolo[4,3-c]pyridine derivatives; pyrazolo[4,3-d][1,2]diazepine derivatives; pyrazol-3-yl-pyrimidine derivatives and fused pyrazol-3-yl-pyranones; pyrazolo[1,5-c]pyrimidin-5-one derivatives; 7-amino-3-ethoxycarbonylpyrazolo[1,5-c]pyrimidin-5(1H)-one; pyridin-4(1H)ones; 4-hydroxypyridin-2(1H)-one and pyrano[3,2-c]pyridinone derivatives; thiazolo[5,4-c]pyridine derivatives; 4-oxo-1,4-dihydropyridazine-3,5-dicarboxylates; heteroaryl substituted pyrimidine derivatives; (pyrido[1,2-a]pyrimidin-3-yl)thiazole-5-carboxylates; and parallel solution-phase synthesis of 1,4-dihydropyridine derivatives.

Dialkyl Acetone-1,3-dicarboxylates and Their Mono- and Bis(dimethylamino)methylidene Derivatives in the Synthesis of Heterocyclic Systems

Reactions of methyl 2‐(benzyloxycarbonyl)amino‐3‐dimethylaminopropenoate and related compounds with hydrazines. Regiospecific synthesis of 1‐substituted‐4‐amino‐substituted‐1H‐pyrazol‐5‐(2H)‐ones

Alkyl 2-(2-benzoyl-2-ethoxycarbonyl-1-ethenyl)amino-3-dimethylaminopropenoates 4a,b were prepared. They react with C-nucleophiles such a 2-pyridinylacetonitrile 5 and methyl-2-quinolinylacetate 8, cyclohexane-1,3-dione 10 and its derivatives 12 and 14, resorcinol derivative 16, 2-naphtol 18, 2-pyranone derivatives 20 and 22, and 4-hydroxypyridin-2(1H)-one 24, to form substituted amino derivatives of quinolizine 6, benzo[c]quinolizine 9, tetrahydrobenzopyran-2-one 11, 13, 15, naphto[2,1-b]pyran-3-one 19, pyranopyranones 21, 23, and pyrano[3,2-c]pyridine 25.

Branko Stanovnik

Papers

A Simple Synthesis of Dimethyl 2‐[(Z)‐3‐Amino‐1‐oxo‐1‐(substituted)but‐2‐en‐2‐yl]fumarates: Potential Intermediates in the Synthesis of Polysubstituted Five‐ and Six‐Membered Heterocycles.

Reactions of Enaminones and Related Compounds with N,N‐Dimethylacetamide Dimethyl Acetal. A Simple One‐Pot Metal‐Free Synthesis of Polysubstituted Benzene Derivatives.

Dialkyl Acetone-1,3-dicarboxylates and Their Mono- and Bis(dimethylamino)methylidene Derivatives in the Synthesis of Heterocyclic Systems

Reactions of methyl 2‐(benzyloxycarbonyl)amino‐3‐dimethylaminopropenoate and related compounds with hydrazines. Regiospecific synthesis of 1‐substituted‐4‐amino‐substituted‐1H‐pyrazol‐5‐(2H)‐ones

Alkyl 2-(2-Benzoyl-2-ethoxycarbonyl-1-ethenyl)amino-3- dimethylaminopropenoates in the Synthesis of Heterocyclic Systems.