49615-28-3Relevant academic research and scientific papers
A detailed study of antibacterial 3-acyltetramic acids and 3-acylpiperidine-2,4-diones
Jeong, Yong-Chul,Bikadi, Zsolt,Hazai, Eszter,Moloney, Mark G.
supporting information, p. 1826 - 1837 (2014/08/18)
Inspired by the core fragment of antibacterial natural products such as streptolydigin, 3-acyltetramic acids and 3-acylpiperidine-2,4-diones have been synthesised from the core heterocycle by direct acylation with the substituted carboxylic acids using a strategy which permits ready access to a structurally diverse compound library. The antibacterial activity of these systems has been established against a panel of Gram-positive and Gram-negative bacteria, with activity mostly against the former, which in some cases is very potent. Data consistent with modes of action against undecaprenylpyrophosphate synthase (UPPS) and/or RNA polymerase (RNAP) for a small subset of the library has been obtained. The most active compounds have been shown to exhibit binding at known binding sites of streptolydigin and myxopyronin at UPPS and RNAP. These systems offer potential for their antibacterial activity, and further demonstrate the use of natural products as biologically validated starting points for drug discovery.
Chemoselective N-acylation via condensations of N-(benzoyloxy)amines and α-ketophosphonic acids under aqueous conditions
Arora, Jasbir Singh,Kaur, Navneet,Phanstiel IV, Otto
, p. 6182 - 6186 (2008/12/22)
(Chemical Equation Presented) A new amide-forming reaction with N-benzoyloxyamines and α-ketophosphonic acids was investigated. A mixed solvent of t-BuOH/water (1:1) at 40°C provided the desired amide in high yield (71-96%). Both phosphonic acids (9, 12, or 13) and their disodium salts (e.g., 10) were shown to react with the respective N-benzoyloxyamines (1b and 4) in excellent yields. The phosphonic acid methyl ester monosodium salt 11 did not react under these conditions. However, compound 11 did provide the desired amide in 22% yield upon addition of 2 equiv of TFA. The N-acylation reaction is highly chemoselective for N-benzoyloxyamines as both aliphatic amines and N-hydroxylamines were shown not to react productively with the α-ketophosphonic acids under the conditions tested. Moreover, the α-ketophosphonic acids are more selective than the related α-ketocarboxylic acid systems, which react with both the N-hydroxylamines and N-benzoyloxyamines. In this regard, this novel phosphonic acid methodology provides a new high-yielding, chemoselective acylating reagent for further study.
Microwave-assisted michael addition of amides to α,β-unsaturated esters under solvent-free conditions
Zare,Hasaninejad,Parhami,Moosavi Zare,Khalafi-Nezhad
, p. 1059 - 1066 (2008/09/21)
Michael addition of amides to α,β-unsaturated esters efficiently proceed in the presence of K2CO3 and tetrabutylammonium bromide (TBAB) as a phase-transfer catalyst under microwave irradiation to afford N-alkylated amides in high yields and short reaction times.
The preparation of functionalized amines and amides using benzotriazole derivatives and organozinc reagents
Katritzky, Alan R.,Strah, Sonja,Belyakov, Sergei A.
, p. 7167 - 7178 (2007/10/03)
Secondary and tertiary amines 6 are conveniently prepared in good yields by reacting organozinc halides with adducts 4, which are derived from the corresponding amines, aldehydes and benzotriazole. The use of organozinc reagents enables the introduction of nitro, cyano or ester functionalities into amine mainframes. This methodology was also used to prepare functionalized amides 8.
Reaction of Chromium (Fischer) Carbenes and Sulfilimines
Alcaide, Benito,Casarrubios, Luis,Dominguez, Gema,Sierra, Miguel A.
, p. 3886 - 3894 (2007/10/02)
The photochemical reactions of alkoxychromium (Fischer) carbenes and sulfilimines lead to imidates in fair to excellent yields.Aromatic, heteroaromatic, and alkylsulfilimines, the latter bearing functional groups such as cyano, sulfone, ether, ester, and dioxolane groups, gave the corresponding imidates in good to excellent yield.However, acyl- and sulfonyl-substituted sulfilimines did not react with chromium carbenes, except for sulfilimines bearing ethoxycarbonyl and phthalimidylamino groups.A variety of differently substituted chromium carbene complexes bearing alkyl, cycloalkyl, styryl, allyl, and alkynyl groups attached either at the carbene carbon or at the oxygen also gave imidates in good yields.For α,β-unsaturated carbenes, the exclusive 1,2-addition of the sulfilimines nitrogen was observed at room temperature, in contrast to the behavior of other nitrogen nucleophiles which are reported to add in 1,4-fashion under these reaction conditions.In turn, optically active imidates of the type ArN=C(OR*)Me can be prepared efficiently by utilizing the corresponding chiral alkoxy group on the carbene moiety.The reactions above also occur in the dark but reaction times are considerably longer.N-Halosulfilimines reacted with alkoxychromium carbenes to yield N-acylsulfilimines instead of the expected N-haloimidates.Based upon a set of thermal and photochemical reactions between N-haloimidates and diphenyl sulfide in the absence of chromium complexes, the complex (CO)5CrNCMe is proposed to be responsible for this novel reaction of N-haloimidates and diphenyl sulfide.
