Thioesterifications Free of Activating Agent and Thiol: A Three-Component Reaction of Carboxylic Acids, Thioureas, and Michael Acceptors

2015 ◽  
Vol 357 (12) ◽  
pp. 2644-2650 ◽  
Author(s):  
Sharada Prasanna Swain ◽  
Yen-Lin Chou ◽  
Duen-Ren Hou
Keyword(s):  
Carboxylic Acids ◽  
Three Component Reaction ◽  
Michael Acceptors ◽  
Activating Agent

Three-Component Reaction between Alkyl Isocyanides, Dialkyl Acetylenedicarboxylates, and Carboxylic Acids

2011 ◽  
Vol 35 (11) ◽  
pp. 661-663 ◽  
Author(s):  
Alireza Hassanabadi ◽  
Mohammad H. Mosslemin ◽  
Sonia Singh ◽  
Seyyed Ali Shaterchi
Keyword(s):  
Carboxylic Acids ◽  
Dialkyl Acetylenedicarboxylates ◽  
Alkyl Isocyanides ◽  
Three Component Reaction

scholarly journals The Flögel-three-component reaction with dicarboxylic acids – an approach to bis(β-alkoxy-β-ketoenamides) for the synthesis of complex pyridine and pyrimidine derivatives

2014 ◽  
Vol 10 ◽  
pp. 394-404 ◽  
Author(s):  
Mrinal K Bera ◽  
Moisés Domínguez ◽  
Paul Hommes ◽  
Hans-Ulrich Reissig
Keyword(s):  
Dft Calculations ◽  
Carboxylic Acids ◽  
Aromatic Compounds ◽  
Dicarboxylic Acids ◽  
Membered Ring ◽  
Simple Synthesis ◽  
Pyrimidine Derivatives ◽  
Three Component Reaction ◽  
Palladium Catalyzed ◽  
Pyridine And Pyrimidine Derivatives

An extension of the substrate scope of the Flögel-three-component reaction of lithiated alkoxyallenes, nitriles and carboxylic acids is presented. The use of dicarboxylic acids allowed the preparation of symmetrical bis(β-ketoenamides) from simple starting materials in moderate yields. Cyclocondensations of these enamides to 4-hydroxypyridine derivatives or to functionalized pyrimidines efficiently provided symmetrically and unsymmetrically substituted fairly complex (hetero)aromatic compounds containing up to six conjugated aryl and hetaryl groups. In addition, subsequent functionalizations of the obtained heterocycles by palladium-catalyzed couplings or by oxidations are reported. We also describe the simple synthesis of a structurally interesting macrocyclic bispyrimidine derivative incorporating a 17-membered ring, whose configuration was elucidated by DFT calculations and by subsequent reactions.

Synthesis of Aminocarbonyl N-Acylhydrazones by a Three-Component Reaction of Isocyanides, Hydrazonoyl Chlorides, and Carboxylic Acids

2014 ◽  
Vol 16 (20) ◽  
pp. 5332-5335 ◽  
Author(s):  
Mariateresa Giustiniano ◽  
Fiorella Meneghetti ◽  
Valentina Mercalli ◽  
Monica Varese ◽  
Francesco Giustiniano ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Hydrazonoyl Chlorides ◽  
Three Component Reaction

Cyclizations of Alkoxyallenes: Mechanisms, Intermediates, ­Products – A Personal Account on Solved and Unsolved Problems with Unique Allene Building Blocks

Synthesis ◽  
2017 ◽  
Vol 49 (15) ◽  
pp. 3291-3302 ◽  
Author(s):  
Hans-Ulrich Reissig ◽  
Reinhold Zimmer
Keyword(s):  
Natural Products ◽  
Carboxylic Acids ◽  
Carbonyl Compounds ◽  
Building Blocks ◽  
Ring Closure ◽  
Pyridine Derivatives ◽  
Personal Account ◽  
Three Component Reaction ◽  
Hydroxylamine Derivatives ◽  
Oxazine Derivatives

The additions of lithiated alkoxyallenes to electrophiles, such as carbonyl compounds, thioketones, imines, and nitrones, provide the expected primary addition products. These alkoxyallene intermediates undergo ring-closure reactions under quite different conditions. Whereas allenyl hydroxylamine derivatives spontaneously cyclize to 1,2-oxazine derivatives, the related allenyl amines, thiols, and alcohols require, with distinct exceptions, promotion by acids, base, silver(I), or gold(I). The different mechanisms of these processes are discussed in this account. The serendipitous discovery of a novel three-component reaction of lithiated alkoxyallenes, nitriles, and carboxylic acids followed by a cyclization to pyridine derivatives is also reported and the mechanism involved is illustrated. This account also compiles exemplary examples of natural products and other compounds prepared by subsequent reactions of alkoxyallene-based cyclization products, but the fascinating ring-closing event of the allenyl intermediates is the main focus of this report.1 Introduction2 Cyclizations of Allenyl Hydroxylamines to 1,2-Oxazine Derivatives3 Cyclizations of Allenyl Amines to Dihydropyrrole Derivatives4 Cyclizations of Allenyl Imines to Pyrroles – Discovery of a New Three-Component Synthesis of Pyridines5 Cyclizations of Allenyl Thiols to Vinylthiiranes and Dihydrothiophene Derivatives6 Cyclizations of Allenyl Alcohols to Dihydrofuran Derivatives7 Conclusions

An efficient tandem approach for the synthesis of functionalized 2-pyridone-3-carboxylic acids using three-component reaction in aqueous media

2014 ◽  
Vol 18 (3) ◽  
pp. 535-543 ◽  
Author(s):  
Saber Mehrparvar ◽  
Saeed Balalaie ◽  
Mahnaz Rabbanizadeh ◽  
Elmira Ghabraie ◽  
Frank Rominger
Keyword(s):  
Carboxylic Acids ◽  
Aqueous Media ◽  
Three Component Reaction
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