15567-95-0Relevant academic research and scientific papers
Hydrolysis of iminium ethers derived from the reaction of ketones with hydroxy azides: Synthesis of macrocyclic lactams and lactones
Forsee, Jennifer E.,Aube, Jeffrey
, p. 4381 - 4385 (1999)
The hydrolysis of iminium ether intermediates formed by a nitrogen insertion sequence involving azido alcohols 1 or 2 and ketones was investigated. Ketones containing 6-12-membered rings were surveyed and shown to provide lactams and lactones in good to excellent overall yield. Reactions employing acetone or 5-nonanone gave similar results, generating analogous amides and esters. The relative amounts of lactone vs lactam produced in a given reaction were found to depend on the structures of the reactants and the pH of the basic media used to hydrolyze the iminium ethers. A mechanism accounting for the formation of each product is discussed in terms of ring strain and the protonation state of ortho ester aminal intermediates.
Cycloalkyl and heterocycloalkyl inhibitors as well as preparation method and application thereof
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Paragraph 0367-0370, (2021/04/26)
The invention relates to cycloalkyl and heterocycloalkyl inhibitors as well as a preparation method and application thereof. Specifically, the compounds disclosed by the invention have a structure as shown in a formula (I). The invention also discloses a preparation method of the compounds and application of the compounds as KRASG12C inhibitors. The compounds have a good selective inhibition effect on KRASG12C, and have better pharmacodynamic and pharmacokinetic properties and lower toxic and side effects.
Metal-Free O-Selective Direct Acylation of Amino Alcohols Through Pseudo-Intramolecular Process
Yokoyama, Soichi,Shibauchi, Hiroshi,Asahara, Haruyasu,Nishiwaki, Nagatoshi
, p. 1125 - 1133 (2019/02/01)
Efficient α-aryl-β-keto ester acylation of amine accompanied by the elimination of ethyl phenylacetate was achieved owing to the pseudo-intramolecular process. The eliminated ethyl phenylacetate could be recycled by conversion into an α-aryl-β-keto ester upon treatment with an acyl chloride in the presence of lithium bis(trimethylsilyl)amide, by which the atom economy considerably increased. Acylation using an α-aryl-β-keto ester is highly sensitive to the bulkiness of the nucleophile, which facilitated the regioselective-acylation of the less hindered amino group in diamine without protecting the other. The transacylation of α-aryl-β-keto ester with N-alkylamino alcohol resulted in chemoselective O-acylation without protecting the amino group because the hydroxy group was attracted to the reaction site of the keto ester by forming an ammonium salt. Transacylation was demonstrated to be a practically useful tool for organic synthesis because this protocol can be conducted under mild conditions with simple manipulations in the absence of any additives such as metal catalyst and base.
Reactions on a Solid Surface. A Simple, Economical, and Efficient Acylation of Alcohols, Amines over Al2O3
Yadav, Veejendra K.,Babu, K. Ganesh
, p. 577 - 580 (2007/10/03)
Al2O3 brings about a rapid acylation of a range of alcohols and amines with acid chlorides and acid anhydrides, respectively. Amines are easily Boc- and Cbz-protected on reaction with Boc-anhydride and Cbz-Cl, respectively. The acylation of phenols is slow enough to allow chemoselective acylation of alcohols and amines in the presence of phenols.
