Heterocyclic Studies. XIII. The Aldol Condensation of 2,3-Dihydro-5-methyl-6-phenyl-4H-1,2-diazepin-4-one and Rearrangement to a Pyridazine<sup>1</sup>

Bly, Ruta K.; Zoll, Estelle C.; Moore, James A.

doi:10.1021/jo01031a005

Cited by 9 publications

(1 citation statement)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Currently, only a few compounds of 2,3‐disubstituted maleic hydrazides have been reported in literature and are suggested to favor specific monolactim forms. Of those reported, such as 2,3‐dimethyl ( 2 , mp 347–351°C) [6], 2‐methyl‐3‐phenyl ( 3 , mp 322–326°C) [7] and the notable monolactim form, 2,3‐diphenyl maleic hydrazide ( 4 , mp 350°C) [8], none have been previously characterized by NMR. …”

Section: Introductionmentioning

confidence: 99%

New heterocycles of 2,3‐diaryl‐substituted maleic hydrazides

Shih

Shih²,

Carson

2011

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

2,3‐Diaryl‐substituted maleic anhydrides were prepared by a modified one‐pot synthesis of Perkin condensation using mixed sodium salts of arylglyoxylic acid and arylacetic acid with acetic anhydride in 1,4‐dioxane. The treatment of these anhydrides with ammonium bicarbonate, or methanolic hydrazine, offered the corresponding 2,3‐diaryl‐substituted maleimides and maleic hydrazides (4,5‐diaryl‐substituted 1,2‐dihydropyridazine‐3,6‐dione), respectively. Evidence obtained from NMR, UV, and mass spectra suggest that 2,3‐diaryl‐substituted maleic hydrazides do not exhibit monolactim forms. Ring contraction of the diaryl‐substituted maleic hydrazide by nitrosation led to the formation of the corresponding maleimide. Interconversion between the corresponding maleic hydrazide and maleimide was observed following equilibrium reaction. Our experiment proposes that the chemistry of 2,3‐diaryl‐substituted maleic hydrazides rarely involves the function of ethylene moiety and resembles that of succinic hydrazine. J. Heterocyclic Chem.,(2011).

show abstract

Section: Introductionmentioning

confidence: 99%

New heterocycles of 2,3‐diaryl‐substituted maleic hydrazides

Shih

Shih²,

Carson

2011

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

The Aldol Condensation

Nielsen

Houlihan²

2011

Organic Reactions

View full text Add to dashboard Cite

The aldol condensation takes its name from aldol (3‐hydroxybutanal) a name introduced by Wurtz who first prepared the beta‐hydroxy aldehyde from acetaldehdye in 1872. The aldol condensation includes reactions producing beta‐hydroxy aldehydes or beta‐hydroxy ketones by self condensations or mixed condensations of aldehydes and ketones as well as reactions leading to alpha, beta‐unsaturated aldehydes or alpha,beta‐unsaturated ketones formed by dehydration of intermediate beta‐aldols or beta‐ketals. The Claisen‐Schmidt condensation is most often taken to be the condensation of an aromatic aldehyde or ketone usually in the presence of a basic catalyst. The term aldol condensation has also been applied to many other condensations involving the reaction of an aldehyde or ketone. These condenations are discussed. The present review includes examples that are solely condensation reactions of aldehydes and ketones.

show abstract