72676-71-2Relevant academic research and scientific papers
Wolff rearrangement of diazo ketones derived from N-p-tolylsulfonyl-protected α- and β-amino acids
Wang, Jianbo,Hou, Yihua
, p. 1919 - 1923 (2007/10/03)
Diazo ketones derived from N-p-tolylsulfonyl (tosyl)-protected α- and β-amino acids have been synthesized and their diazo decomposition under standard Wolff rearrangement conditions, PhCO2Ag-Et3N-MeOH, has been investigated. It is observed that, under these conditions, several different reaction pathways, including direct carbene N-H insertion, are possible. The reaction is markedly affected by the N-protecting group, the substrate structure and solvent. For those diazo ketones derived from N-tosyl-protected β-amino acids, the diazo decomposition with anhydrous THF as solvent and PhCO2Ag dissolved in Et3N as catalyst gives the corresponding 5-substituted pyrrolidinones in excellent yields.
SYNTHESIS AND REACTIONS OF DIAZOCARBONYL COMPOUNDS. I. REACTION OF 1-DIAZO-3-, 1-DIAZO-4-, AND 1-DIAZO-5-PHTHALIMIDOALKAN-2-ONES WITH HYDRAZINE HYDRATE. SYNTHESIS OF 1-DIAZO-3-, 1-DIAZO-4-, AND 1-DIAZO-5-ARENESULFAMOYLALKAN-2-ONES
Sipyagin, A. M.,Kartsev, V. G.
, p. 353 - 361 (2007/10/02)
The reaction of hydrazine hydrate with 1-diazo-3-, 1-diazo-4-, and 1-diazo-5-phthalimidoalkan-2-ones containig a substituent at the α position to the phthalimide group in the hydrocarbon chain leads to the formation of 1-diazo-3- and 1-diazo-4-(2-hydrazid
ACETOLYSIS OF α'-SULPHONAMIDO α-CHLORO AND α-DIAZO KETONES. A CONVENIENT SYNTHESIS OF 3-AZETIDINONES
Pusino, Alba,Saba, Antonio,Desole, Giuseppe,Rosnati, Vittorio
, p. 33 - 36 (2007/10/02)
Acetolysis of tertiary sulfonyl amides 1b,d leads to chlorine cinesubstitution exclusively, while in the case of the secondary amides 1a,c,e, only products of β-elimination are obtained.Acetolysis of the related diazo ketones 2b,d bearing a tertiary nitrogen atom, leads to normal substitution of the diazo group exclusively, whereas with the corresponding secondary amides 2a,c,e a concurrent cyclization to the 3-azetidinones 9, 12 and 15 is observed.By decomposition of the same diazoketones 2a,c,e in the presence of catalytic amounts of Cu(CF3COCHCOCF3)2, the above 3-azetidinones are obtained in excellent yields.
Antitumor agents: diazomethyl ketone and chloromethyl ketone analogues prepared from N-tosyl amino acids
Sajadi,Kashani,Loeffler,Hall
, p. 275 - 278 (2007/10/02)
Diazomethyl ketone and chloromethyl ketone analogues prepared from N-tosyl amino acids have been synthesized and tested for antitumor activity in Ehrlich ascites carcinoma and P-388 lymphocytic leukemia screens in mice. The N-tosyl chloromethyl ketone ana
