162733-63-3Relevant academic research and scientific papers
Chemoselective Cleavage of Acylsulfonamides and Sulfonamides by Aluminum Halides
Sang, Dayong,Dong, Bingqian,Liu, Yunfeng,Tian, Juan
, p. 3586 - 3595 (2022/02/25)
The chemoselective cleavage of C-N bonds of amides, sulfonamides, and acylsulfonamides by aluminum halides is described. AlCl3and AlI3display complementary reactivities toward N-alkyl and N-acyl moieties. N-Alkylacylsulfonamides, sec
Cu-catalyzed conversion of propargyl acetates to e-a,β-unsaturated amides via ketenimine formation with sulfonyl azides
Kumar, Yalla Kiran,Kumar, Gadi Ranjith,Reddy, Maddi Sridhar
, p. 823 - 828 (2014/04/03)
The reaction between readily accessible propargyl acetates and sulfonyl azides in the presence of CuI catalyst yields trans-a,β-unsaturated Ntosylamides via N-sulfonyl ketenimine formation followed by a probable 1,3- OAc migration ([3,3]-sigmatropic rearrangement). The reaction is very general, allowing all kinds of substitution, including alkyl, aryl (electrondonating, -withdrawing, and -neutral), heteroaryl, and vinyl groups, on the Cterminal of acrylamide. Also, the method affords the products at ambient temperature with excellent diastereoselectivity in moderate to good yields.
Direct acyl substitution of carboxylic acids: A chemoselective o- to N-acyl migration in the traceless staudinger ligation
Kosal, Andrew D.,Wilson, Erin E.,Ashfeld, Brandon L.
supporting information, p. 14444 - 14453,10 (2020/09/16)
A chlorophosphite-modified, Staudinger-like acylation of azides involving a highly chemoselective, direct nucleophilic acyl substitution of carboxylic acids is described. The reaction provides the corresponding amides with analytical purity in 32-97 % yield after a simple aqueous workup without the need for a pre-activation step. The use of chlorophosphites as dual carboxylic acid-azide activating agents enables the formation of acyl C-N bonds in the presence of a wide range of nucleophilic and electrophilic functional groups, including amines, alcohols, amides, aldehydes, and ketones. The coupling of carboxylic acids and azides for the formation of alkyl amides, sulfonyl amides, lactams, and dipeptides is described. Copyright
4-endo-trig cyclization processes using bis(collidine)bromine(i) hexafluorophosphate as reagent: Preparation of 2-oxetanones, 2-azetidinones, and oxetanes
Homsi, Fadi,Rousseau, Gerard
, p. 81 - 85 (2007/10/03)
Reaction in methylene chloride of bis(collidine)bromine(I) hexafluorophosphate with α,β-unsaturated acids and α,β-unsaturated N- sulfonamides was found to lead diastereospecifically to the corresponding 2- oxetanones and 2-azetidinones in moderate yields (23-60%), by an almost unknown 4-endo cyclization. This process allow the synthesis of these interesting classes of products in one step from common substrates. Similarly, the reaction of cinnamic alcohols led, by the same cyclization procedure, to oxetanes (20-36%); the presence of a gem-dimethyl group in α of the alcohol function appeared beneficial.
Tin for Organic Synthesis, 11. A Mild and Effective Synthesis of α,β-unsaturated Carboxamides and Sulfonamides by Electrophilic Substitution of Alkenylstannanes with Isocyanates
Niestroj, Michael,Neumann, Wilhelm P.,Thies, Olaf
, p. 1131 - 1136 (2007/10/02)
A new and effective method for the preparation of a variety of olefinic carboxamides 6a-k and N-(4-methylphenylsulfonyl)carboxamides 7a-d is described.The reaction of aryl and alkyl isocyanates 4a-c or 4-methylphenylsulfonyl isocyanate 5 with 1-alkenyltrialkylstannanes 1a-e and di-1-alkenyldibutylstannanes 2a-c in the presence of aluminium trichloride provides the corresponding N-aryl-substituted olefinic carboxamides 6a-k or the N-(4-methylphenylsulfonyl)-substituted olefinic carboxamides 7a-d in good yields.The stannyl moiety is superior to hydrogen as a leaving group and enables electrophilic ipso substitution at the vinylic system.In the case of di-1-alkenyldibutylstannanes the substitutions are also stereospecific, whereas the reactions of 1-alkenyltrialkylstannanes with isocyanates proceed with partial isomerisation. - Key Words: Electrophilic vinylic substitution / Isocyanates / α,β-Unsaturated amides, synthesis of / Carbodestannylation / Alkenylstannanes, applications of
