3532-37-4Relevant academic research and scientific papers
Electrodimerization ofN-Alkoxyamides for the Synthesis of Hydrazines
Nasier, Abudulajiang,Chang, Xihao,Guo, Chang
, p. 16068 - 16076 (2021/09/18)
An efficient and valuable N-N dimerization reaction ofN-alkoxyamides is reported under undivided electrolytic conditions. This electrochemical strategy provides a powerful way to access a wide range of advanced, highly functionalized hydrazines. Remarkably, anN-centered radical generated from the cleavage of the N-H bond under electrolytic conditions plays a crucial role in this transformation. Furthermore, variousN-alkoxyamides bearing different substituents are suitable in this transformation, furnishing the corresponding hydrazines in up to 92% yield.
Carboxyesterase polypeptides for amide coupling
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Page/Page column 61-62; 65-66; 79-81, (2021/05/28)
The present invention provides engineered carboxyesterase enzymes having improved properties as compared to a naturally occurring wild-type carboxyesterase enzymes, as well as polynucleotides encoding the engineered carboxyesterase enzymes, host cells capable of expressing the engineered carboxyesterase enzymes, and methods of using the engineered carboxyesterase enzymes in amidation reactions.
Synthesis of biaryl imino/keto carboxylic acids via aryl amide directed C-H activation reaction
Zhang, Nana,Yu, Qingzhen,Chen, Ruixue,Huang, Jianhui,Xia, Yeqing,Zhao, Kang
, p. 9464 - 9466 (2013/10/01)
A novel Pd-catalysed C-H activation reaction for the synthesis of biaryl imino/keto carboxylic acids is developed. This reaction underwent aryl amide directed C-H activation ortho-acylation followed by ring closing and ring opening processes to give a range of biaryl imino/keto carboxylic acids. Our methodology features the utilization of a cheap and green oxidant (TBHP) as well as readily available aldehydes.
Conversion of primary alcohols and aldehydes into methyl esters by ruthenium-catalysed hydrogen transfer reactions
Owston, Nathan A.,Nixon, Tracy D.,Parker, Alexandra J.,Whittlesey, Michael K.,Williams, Jonathan M. J.
scheme or table, p. 1578 - 1581 (2009/12/22)
Alcohols and aldehydes are oxidised to the corresponding methyl esters by reaction with methanol in the presence of crotononitrile as a hydrogen acceptor using a catalyst combination of Ru(PPh3)3(CO)H2 with xantphos. Georg Thieme Verlag Stuttgart.
SN2 substitution reactions at the amide nitrogen in the anomeric mutagens, N-acyloxy-N-alkoxyamides
Cavanagh, Katie L.,Glover, Stephen A.,Price, Helen L.,Schumacher, Rhiannon R.
experimental part, p. 700 - 710 (2010/02/16)
N-Acyloxy-N-alkoxyamides 1a are unusual anomeric amides that are pyramidal at the nitrogen because of bis oxyl substitution. Through this configuration, they lose most of their amide character and resemble -haloketones in reactivity. They are susceptible to SN2 reactions at nitrogen, a process that is responsible for their mutagenic behaviour. Kinetic studies have been carried out with the nucleophile N-methylaniline that show that, like SN2 reactions at carbon centres, the rate constant for SN2 displacement of carboxylate is lowered by branching to the nitrogen centre, or bulky groups on the alkoxyl side chain. Branching or bulky groups on the carboxylate leaving group, however, do not impact on the rate of substitution, which is mostly controlled by the pKA of the departing carboxylate group. These results are in line with computed properties for the model reaction of ammonia with N-acetoxy-N-methoxyacetamide but are in contrast to the role of steric effects on their mutagenicity. CSIRO 2009.
Hindered ester formation by SN2 azidation of N-acetoxy-N-alkoxyamides and N-alkoxy-N-chloroamides-novel application of HERON rearrangements
Glover, Stephen A.,Mo, Guoning
, p. 1728 - 1739 (2007/10/03)
Treatment of N-acetoxy-N-alkoxyamides or N-alkoxy-N-chloroamides with sodium azide in aqueous acetonitrile results in SN2 displacement of chloride and the formation of reactive N-alkoxy-N-azidoamides. The reaction with N-acetoxy-N-benzyloxybenzamide has been studied kinetically (k294 = 2 L mol-1 s-1) and azidation of N-formyloxy-N-methoxyformamide has been modeled computationally at the pBP/DN*//HF/6-31G* level of theory. The anomeric amides N-alkoxy-N-azidoamides decompose intermolecularly and spontaneously to esters and two equivalents of nitrogen. This extremely exothermic process facilitates the formation, in excellent yields, of highly hindered esters.
Preparation and thermal decomposition of N,N'-diacyl-N,N'-dialkoxyhydrazines: Synthetic applications and mechanistic insights
De Almeida, Mauro V.,Barton, Derek H. R.,Bytheway, Ian,Ferreira, J. Albert,Hall, Michael B.,Liu, Wansheng,Taylor, Dennis K.,Thomson, Lisa
, p. 4870 - 4874 (2007/10/02)
Oxidation of various O-alkyl hydroxamates 1 where R1 was a keto-methoxime, benzoyl, aryl, or alkyl group with ceric ammonium nitrate (CAN) or nickel peroxide (NiO2·H2O) leads to the corresponding esters in high yield. This augurs well for the facile synthesis of highly hindered esters. Dimers of type 2 were identified as intermediates in these oxidations, and a combination of experimental and theoretical results suggest that these dimers decompose in a stepwise 1,1-elimination manner via intermediate nitrenes to furnish the esters and not via a stepwise 1,2-elimination sequence as previously thought.
