A Novel Synthesis of Hydrazine Derivatives via a Three-Component Procedure

Islami, Mohammad Reza; Gholami, Nader; Dehooei, Abolfazl; Amiri, Asghar

doi:10.1080/104265090969540

Cited by 7 publications

(1 citation statement)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reaction of the 1:1 triphenylphosphine-dialkyl acetylenedicarboxylate adducts with N-H acids such as imidazole, benzimidazole, benzotriazole [70], 2-aminobenzimidazole [71], indole, 2-acetylpyrrole [72], hydantoin [73], 2-hydroxy benzimidazole [74], 2-aminothiazole [75], harman and harmin [76], 2-benzoxazolinone [77], trifluoroacetamide [78], acetylated acetaminophen [79], N-substituted aryl hydrazine [80], and 1,2-phenylenediamine [81] have provided new stabilized phosphorus ylides.…”

Section: Reaction Of Triphenylphosphine Dialkyl Acetylenedicarboxylamentioning

confidence: 99%

Synthesis and Reactions of Stabilized Phosphorus Ylides

Ramazani

Kazemizadeh

Ahmadi³

et al. 2008

COC

106

View full text Add to dashboard Cite

Stabilized phosphorus ylides, versatile intermediates in synthetic organic chemistry can be prepared by the novel reaction of dialkyl acetylenedicarboxylates (DAAD), triphenylphosphine (TPP) and acids such as phenols, imides, amides, enols, oximes and alcohols. The reaction involves an intermediate formed by the 1:1 conjugate addition reaction of the TPP to DAAD and concomitant protonation of the intermediate by an acid leads to vinyltriphenylphosphonium salts. The salts are unstable intermediates and converted to stabilized phosphorus ylides via Michael addition reaction. The stabilized phosphorus ylides are able to take part in the normal intramolecular Wittig reactions but they are not generally able to participate in the normal intermolecular Wittig reactions. The intermolecular Wittig reactions of the ylides are observed only with highly electron-poor carbonyl groups such as indane-1,2,3-trione. The ylides are converted to electron-poor alkenes via elimination of TPP in solvent-free conditions. Almost all of the final products are valuable families of compounds. †Dedicated to Professor Issa Yavari on the occasion of his 59th birthday.

show abstract

Section: Reaction Of Triphenylphosphine Dialkyl Acetylenedicarboxylamentioning

confidence: 99%

Synthesis and Reactions of Stabilized Phosphorus Ylides

Ramazani

Kazemizadeh

Ahmadi³

et al. 2008

COC

106

View full text Add to dashboard Cite

show abstract

A Novel Synthesis of Hydrazine Derivatives via a Three‐Component Procedure.

et al. 2006

View full text Add to dashboard Cite

Hydrazines Q 0150A Novel Synthesis of Hydrazine Derivatives via a Three-Component Procedure.-Phenylhydrazine derivatives (I) are condensed with acetylenic esters (II) in the presence of triphenylphosphine providing a rapid synthesis of hydrazines (IV). Readily available starting materials, short reaction times, as well as the good to high yields of the final products are the advantages of this one-pot procedure, compared to previously reported methods. -(ISLAMI*, M. R.; GHOLAMI, N.; DEHOOEI, A.; AMIRI, A.; Phosphorus, Sulfur Silicon Relat.

show abstract