103239-04-9Relevant academic research and scientific papers
Unexpected Formation of 2,2-Dichloro-N-(chloromethyl)acetamides during Attempted Staudinger 2,2-Dichloro-β-lactam Synthesis
Deketelaere, Sari,Van Den Broeck, Elias,Cools, Lore,Deturck, Daan,Naeyaert, Hannes,Van Hecke, Kristof,Stevens, Christian V.,Van Speybroeck, Veronique,D'hooghe, Matthias
, p. 5823 - 5830 (2021/11/17)
In the quest for 3,3-dichloro-β-lactam building blocks, the serendipitous formation of 2,2-dichloro-N-(chloromethyl)acetamides was observed. This peculiar reactivity was investigated in detail, both experimentally and computationally by means of Density Functional Theory (DFT) calculations. 2,2-Dichloro-N-(chloromethyl)acetamides were thus shown to be formed experimentally through reaction of 2,2-dichloroacetyl chloride with glyceraldehyde-derived imines, i. e. (2,2-dimethyl-1,3-dioxolan-4-yl)methanimines, bearing aromatic N-substituents, in the presence as well as in the absence of a base. Deployment of aliphatic imines, however, resulted in complex reaction mixtures, pointing to the importance of a stabilizing aromatic substituent at nitrogen. The DFT results indicate that the substituents can alter the governing equilibria on the one hand and intrinsic barrier heights for the different routes on the other hand, showing that these are controlling the reaction outcome. Furthermore, the 2,2-dichloro-N-(chloromethyl)acetamides proved to be rather unstable in solution and thus difficult to isolate. Nonetheless, their molecular structure was confirmed by means of NMR analysis of several purified analogs and X-ray study of a 4-methoxyphenyl derivative.
An Expeditious Route for the Synthesis of Oxazepine Triazolo-β-Lactams through Intramolecular Metal-Free [3 + 2] Azide-Alkyne Cycloaddition
Yadav, Ram N.,Chandra, Sunena,Paniagua, Armando,Hossain, Md. Firoj,Banik, Bimal Krishna
, p. 654 - 657 (2020/05/25)
A copper-free intramolecular azide-alkyne cycloaddition reaction of 4-hydroxymethyl-β-lactam with sodium azide has been described. The present approach involves the incorporation of an alkyne moiety through O-alkynylation of 3-hydroxy β-lactam with variou
Reactivity of 3-Oxo-β-lactams with Respect to Primary Amines—An Experimental and Computational Approach
Piens, Nicola,Goossens, Hannelore,Hertsen, Dietmar,Deketelaere, Sari,Crul, Lieselotte,Demeurisse, Lotte,De Moor, Jelle,Van den Broeck, Elias,Mollet, Karen,Van Hecke, Kristof,Van Speybroeck, Veronique,D'hooghe, Matthias
, p. 18002 - 18009 (2017/12/13)
The reactivity of 3-oxo-β-lactams with respect to primary amines was investigated in depth. Depending on the specific azetidin-2-one C4 substituent, this reaction was shown to selectively produce 3-imino-β-lactams (through dehydration), α-aminoamides (thr
Decarboxylative Mannich reactions
Boehm, Maximillian,Proksch, Kerstin,Mahrwald, Rainer
supporting information, p. 1046 - 1049 (2013/03/14)
p-Methoxyphenylimines obtained from enolizable aldehydes react in the absence of catalysts at room temperature with β-keto carboxylic acids through a decarboxylative Mannich reaction. The Mannich products were obtained with a high degree of anti selectivity. By use of chiral oxygen-containing aldehydes, operationally simple access to aminohydroxylated polyketide substructures is possible. The results of catalyst-free, decarboxylative Mannich reactions of enolizable imines are described. When the reaction is performed with imines obtained from chiral aldehydes, access to optically pure Mannich products is possible. Copyright
An efficient three-component synthesis of homoallylic amines catalysed by MgI2 etherate
Wang, Yanping,Liu, Yingshuai,Hu, Shenghui,Zhang, Xingxian
experimental part, p. 21 - 24 (2012/03/27)
A three-component reaction of aldehydes, amines and allyltributylstannane was efficiently carried out to afford the corresponding homoallylic amine derivatives in the presence of 20 mol% of MgI2 etherate [(MgI 2?(OEt2)n] under mild and neutral reaction conditions in good to excellent yields.
MICROWAVE-INDUCED ORGANIC REACTION ENHANCEMENT CHEMISTRY. 4 CONVENIENT SYNTHESIS OF ENANTIOPURE α-HYDROXY-β-LACTAMS
Banik, Bimal K.,Manhas, Maghar S.,Kaluza, Zbignew,Barakat, Khaled J.,Bose, Ajay K.
, p. 3603 - 3606 (2007/10/02)
A convenient and rapid synthesis of enantiopure α-hydroxy-β-lactams using microwave-induced organic reaction enhancement chemistry has been developed.Reactions in domestic microwave ovens, which are very convenient and economical for small scale work in research or teaching laboratories, can also be conducted on a preparative scale of 100 - 500 g in simple beakers or flasks. Key Words: α-Hydroxy-β-lactams, microwave-induced organic reactions, enantiospecific synthesis
Stereochemical Aspects of the Bose Reaction for α-Amino-β-lactam Synthesis
Manhas, Maghar S.,Veen, James M. van der,Wagle, Dilip R.,Hegde, Vinod R.,Bari, Shamsher S.,et al.
, p. 1095 - 1104 (2007/10/02)
Stereochemical aspects of the Bose reaction (formation of α-azido-β-lactams from an activated form of azidoacetic acid and imino compounds in the presence of a base) are examined.Substituted β-lactams prepared by stereocontrolled synthesis (including enantiospecific synthesis) are shown to be useful intermediates for β-lactam antibiotics, sugars, alkaloids and other natural products.A stereospecific synthesis of an optically active 3-aminosugar related to gentosamine starting from a β-lactam synthon is described.
