Four-component Synthesis of 1,3,4-Oxadiazole Derivatives from (N-Isocyanimino)triphenylphosphorane, (E)-Cinnamic Acids, Acetaldehyde and Secondary Amines

Ramazani, Ali; Ahmadi, Yavar; Nasrabadi, Fatemeh Zeinali

doi:10.1515/znb-2011-0211

Cited by 2 publications

(2 citation statements)

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“…The procedure is fast, high yielding, and very clean, as the only byproducts are water and TPPO. Very soon, the scope of the reaction was extended to the use of cinnamic, − phenylacetylene, − and peptidic , acids, while primary ,− and peptidic amines , also participate, although giving slightly lower yields. Substituted benzyldehydes, , aromatic dialdehydes, furfural, acetaldehyde, , and cinnamaldehyde , readily react as carbonyl components.…”

Section: Oxadiazole Synthesis By Four-component Reactionsmentioning

confidence: 99%

“…Very soon, the scope of the reaction was extended to the use of cinnamic, − phenylacetylene, − and peptidic , acids, while primary ,− and peptidic amines , also participate, although giving slightly lower yields. Substituted benzyldehydes, , aromatic dialdehydes, furfural, acetaldehyde, , and cinnamaldehyde , readily react as carbonyl components. On the other hand, ketones are restricted to be cyclic ,− or electron-deficient α-halo ketones, , α-acyl(thi)oxy propanones, ,,, and biacetyl …”

Section: Oxadiazole Synthesis By Four-component Reactionsmentioning

confidence: 99%

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One Reacts as Two: Applications of N-Isocyaniminotriphenylphosphorane in Diversity-Oriented Synthesis

et al. 2020

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N-Isocyaniminotriphenylphosphorane (NIITP) is a functionalized isonitrile that has been extensively applied in a variety of organic reactions during the last two decades. This Review summarizes the most important applications in organic synthesis of this versatile reactant, with the focus posed on mechanistic and methodological aspects allowing the generation of molecular diversity. NIITP combines the reactivity of isonitriles with that of phosphoranes to enable chemical transformations employed in the construction of compound libraries. Here, we cover from the initial applications of NIITP in the Nef isocyanide reaction to further derivations that render a variety of heterocyclic scaffolds. The presence of the isonitrile moiety in this singular compound makes possible the double addition of nucleophiles and electrophiles, which followed by inter(intra)molecular aza-Wittig type transformations enable several multicomponent and tandem processes. In particular, we stress the impact of NIITP in oxadiazole chemistry, from the early two-component transformations to recent examples of multicomponent reactions that take place in the presence of suitable electrophiles. In addition, we briefly describe the role of NIITP chemistry in generating skeletal and conformational diversity in cyclic peptides. The reaction of NIITP with alkynes is thoroughly revised, with particular emphasis on silver-catalyzed processes that have been developed in the last years. Biomedicinal applications of some reaction products are also mentioned along with a perspective of future applications of this reactant.

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Section: Oxadiazole Synthesis By Four-component Reactionsmentioning

confidence: 99%

Section: Oxadiazole Synthesis By Four-component Reactionsmentioning

confidence: 99%

One Reacts as Two: Applications of N-Isocyaniminotriphenylphosphorane in Diversity-Oriented Synthesis

et al. 2020

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A Half‐Century of the Ugi Reaction: Modified Variants

Ullrich

Kazmaier

2023

Organic Reactions

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The classic Ugi reaction is a four‐component coupling process involving a carboxylic acid, a carbonyl compound, an amine, and an isocyanide, resulting in an N ‐acylamino acid amide product. Modified Ugi reactions employ special, often multifunctional, reaction components, and can involve fewer than or more than four components. This reaction exhibits broad scope and can be used to prepare complex heterocycles. As a result, this method has been employed to prepare diverse libraries of structurally related products, and in addition, is often applied to the synthesis of drugs, drug‐like molecules, and natural products. Applications in target‐directed synthesis are presented, as are comparisons to other related multicomponent reactions and heterocycle syntheses; modifications leading to achiral heteroaromatic ring systems are not included. This chapter covers the literature from the early days of the Ugi reaction in 1961 through the end of 2012.

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Four-component Synthesis of 1,3,4-Oxadiazole Derivatives from (N-Isocyanimino)triphenylphosphorane, (E)-Cinnamic Acids, Acetaldehyde and Secondary Amines

Cited by 2 publications

References 29 publications

One Reacts as Two: Applications of N-Isocyaniminotriphenylphosphorane in Diversity-Oriented Synthesis

One Reacts as Two: Applications of N-Isocyaniminotriphenylphosphorane in Diversity-Oriented Synthesis

A Half‐Century of the Ugi Reaction: Modified Variants

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