17437-51-3Relevant academic research and scientific papers
A PARTICULARLY CONVENIENT ONE-POT SYNTHESIS OF N-ALKOXYCARBONYL, N-ACYL AND N-AROYL SUBSTITUTED IMINOPHOSPHORANES; IMPROVED PREPARATION OF AZIDOFORMATES, AROYL AND ALKANOYL AZIDES; AN ALTERNATIVE ROUTE TO COMPLEX AMIDES
Froeyen, Paul
, p. 161 - 172 (2007/10/02)
Chloroformates and acid chlorides react smoothly with sodium azide in acetone at 0 deg C, forming azidoformates, aroyl and alkanoyl azides in very high yield.With triphenylphosphine or other phosphines present in the reaction mixture, the forming azides are intercepted, leading directly to the corresponding N-alkanoyl, N-aroyl, N-alkoxycarbonyl, and N-aryloxycarbonyliminophosphoranes.N-acyliminophosphoranes react with n-butyllithium forming anions which react readily with electrophiles, e.g., carbonyl compounds, forming highly substituted iminophosphoranes.The phosphonium group is effortlessly removed from the latter compounds by acid hydrolysis forming the corresponding amides in high yield.Key words: Synthesis; iminophosphoranes; aroyl azides; alkanoyl azides; complex amides.
Preparation and Synthetic Applications of Iminophosphoranes Derived from o-Substituted Arylazides: Preparation of PyrazoloIndazole, 4H-3,1-Benzoxazine and Quinoline Derivatives. Crystal structure of 2--4-methylquino
Molina, Pedro,Conesa, Carlota,Alias, Asuncion,Arques, Antonio,Velasco, Maria D.,et al.
, p. 7599 - 7612 (2007/10/02)
The Staudinger reaction of several ortho-substituted arylazides with triphenylphosphine has been studied.The reaction product is found to be strongly dependent on the nature of the ortho-substituent.The Aza Wittig-type reaction of iminophosphorane derived
A convenient synthesis of triphenylphosphine acylimides using N-lithiated triphenylphosphine imide
Cristau,Manginot,Torreilles
, p. 382 - 384 (2007/10/02)
A series of triphenylphosphine acylimides and N-(triphenylphosphoranylidene)carbamates have been readily prepared by direct acylation of the N-lithiated triphenylphosphine imide.
Ester of (triarylphosphoranylidene)carbamic acid having diuretic and ability to lower plasma renin properties
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, (2008/06/13)
Novel triarylphosphinimide derivatives having the formula STR1 wherein R1, R2 and R3 are each at the ortho or meta position, represent mono- or disubstituents and are selected from the group consisting of hydrogen, alkyl(C1 -C3), alkoxy(C1 -C3), trifluoromethyl and halogen; and R4 is selected from the group consisting of alkyl(C1 -C3), alkenyl(C2 -C3), alkynyl(C2 -C4), cycloalkyl(C3 -C5), cycloalkyl(C3 -C6)methyl, 4-oxopentyl, 3-tetrahydrofuranyl, 2,3-dihydro-1H-inden-1-yl, 1-alkyl(C1 -C3)cyclopentyl, trans-2-alkyl(C1 -C3)cyclopentyl, trans-2-alkoxy(C1 -C3)cyclopentyl, 1-cyclopropylethyl, 2-methylcyclopropylmethyl, dicyclopropylmethyl, 2-, 3- or 4-pyridinylmethyl, 2-cyclopenten-1-yl, tetrahydro-2H-pyran-4-yl and cis and trans-2-methoxycyclohexyl; with the proviso that when R4 is alkyl(C1 -C3), R1, R2 and R3 may not each be hydrogen STR2 wherein R1, R2 and R3 are each at the ortho or meta position and are selected from hydrogen and alkyl(C1 -C3), and X is an acid addition salt; processes for producing them, compositions containing them, and methods for using them in mammals to effect diuresis; to lower plasma renin levels and to increase cardiac contractility.
Synthesis of N-Acyl-, N-Sulfonyl-, and N-Phosphinylphospha-λ5-azenes by a Redox-Condensation Reaction Using Amides, Triphenylphosphine, and Diethyl Azodicarboxylate
Bittner, Shmuel,Assaf, Yonit,Krief, Penina,Pomerantz, Martin,Ziemnicka, Barbara T.,Smith, Christina G.
, p. 1712 - 1718 (2007/10/02)
The reaction of phosphines and amides with diethyl azodicarboxylate (DAD) produced phospha-λ5-azenes.Thus aromatic amides and those aliphathic amides with electron-withdrawing substituents gave N-acyl-P,P,P-triphenylphospha-λ5-azenes (5) when triphenylphosphine (TPP) was employed.Both aryl- and alkylsulfonamides reacted with TPP and DAD to produce the N-sulfonylphospha-λ5-azenes (9).Diphenylphosphinamide (10) and ethyl carbamate (12) also produced the respective phosphazenes (11 and 13) with TPP and DAD.Secondary carboxamides and sulfonamides did not react with TPP and DAD.The reaction of triethyl phosphite with sulfonamides in the presence of DAD produced the phosphorimidates (20) in an analogous reaction, along with the corresponding N,N-diethylsulfonamides and the deethylated adduct of triethyl phosphite and DAD (23).Triethyl phosphite-DAD failed, however, to give a phosphorimidate with carboxamides but gave, instead, the rearranged adduct of DAD and triethyl phosphite (19).Tris(dimethylamino)phosphine reacted with sulfonamides and DAD but the products were the corresponding ethyl N-sulfonylcarbamates (26) rather than the phosphazenes.Tris(dimethylamino)phosphine reacted with azodicarbonamide (a molecule which contains both the azo and carboxamide groups) with the production of N,N-dimethylurea, again without formation of the phosphazene.Finally, the reaction of triphenylarsine with benzenesulfonamide and DAD produced N-(phenylsulfonyl)triphenylarsa-λ5-azene (30) but triphenylstibene with DAD and benzenesulfonamide only gave triphenylstibene oxide.Mechanistic possibilities for these reactions are also discussed.
