Three-component reaction between triphenylphosphine, dialkyl acetylenedicarboxylates and urea or N-methylurea

Abstract

The stabilized phosphoranes, obtained from the three-component reaction between dialkyl acetylenedicarboxylates and urea or N-methylurea in the presence of triphenylphosphine, undergo a smooth reaction in boiling toluene to produce iminophosphoranes in good yields. Under the same reaction conditions, the phosphorane obtained from N-methylurea and dimethyl acetylenedicarboxylate yields methyl 1-methyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylate.

Preparation of Stabilized Phosphorus Ylides via Multicomponent Reactions and Their Synthetic Applications

“…The 1 H, 13 C, and 31 P NMR spectra of ylides (73) are consistent with the presence of two geometric isomers (Scheme 21) [82]. [90], trifluoroacetamide [91], acetylated acetaminophen [92], N-substituted aryl hydrazine [93], and 1,2-phenylenediamine [94], 3,6-dibromocarbazole [95], phenylhydrazones [96], N-methylurea [97], arylsulfonamides [98], pyrazole and indazole [99], imidazolidine-2-thione [100], triazoles and pyrroles [101], phenothiazine [102], 6-chloro-2-benzoxazolethiol and 2-chloro-phenothiazine [103], 6-azauracil [104], 1-amino-anthraquinone and 1,5-diphenylcarbazone [105], diaryltriazenes and electron-poor primary arylamines [106], have provided new stabilized phosphorus ylides.…”

“…Quinolines are interesting synthetic targets because they act as building blocks for a large number of natural products. Dialkyl 1,2-dihydroquinoline-2,3-dicarboxylates (97) are formed in a one-pot reaction from amide derivatives of 2-aminobenzaldehyde (95), DAAD (2) and TPP (1) in CH 2 Cl 2 in high yields (Scheme 29) [124,125].…”

An Approach to P=N Bond Formation: Straightforward Synthesis of Arylurea‐Derived Phosphazenes via Condensation of Ph3P=O withN‐Monosubstituted Arylureas

“…Two general preparative methods to access phosphazenes include the Staudinger reaction and the Kirsanov reaction . More recently, Yavari, Norris, Sundberg, Onys′ ko, Amstrong, Cristau, and Morita have developed methods for phosphazene preparation. Although these methods have been extensively studied, access towards arylurea‐derived phosphazenes remains a challenging endeavor.…”

A Facile Route to Diastereomeric Phosphorus Ylides. Chemoselective Synthesis of Dialkyl (E)-2-[1-(2-Oxocyclopentylidene)ethyl]-2-butenedioates

“…In recent years the three-component reactions of triphenylphosphine, electron-deficient derivatives and ZH -acids (Z=C, O, N, S) that leads to phosphorus ylides have been reported by Yavari et al . [ 10 , 11 , 12 , 13 , 14 , 15 ]. We here report the reaction of 2-acetylcyclopentanone ( 2 , acting as a CH-acid) and dialkyl acetylenedicarboxylates 1 in the presence of triphenylphosphine.…”