10264-26-3Relevant academic research and scientific papers
Enzymatic Method for N-Acyl Homoserine Lactones Synthesis Using Immobilized Candida antarctica Lipase
Vázquez-Martínez, Juan,Nieto-álvarez, Edgar,Ramírez-Chávez, Enrique,Molina-Torres, Jorge
, p. 62 - 67 (2018)
Abstract: An enzymatic method to produce N-acyl homoserine lactones (AHLs) is described. This report represents the first example of the synthesis of bioactive AHLs using immobilized Candida antarctica lipase as the catalyst. The reaction yields, evaluate
Development of a triazinedione-based dehydrative condensing reagent containing 4-(dimethylamino)pyridine as an acyl transfer catalyst
Liu, Jie,Fujita, Hikaru,Kitamura, Masanori,Shimada, Daichi,Kunishima, Munetaka
supporting information, p. 4712 - 4719 (2021/06/11)
A new triazinedione-based reagent, (N,N′-dialkyl)triazinedione-4-(dimethylamino)pyridine (ATD-DMAP) was developed for the operationally simple dehydrative condensation of carboxylic acids. This reagent comprises an ATD core and DMAP as the leaving group, which is liberated into the reaction system to accelerate acyl transfer reactions. Upon adding ATD-DMAP to a mixture of carboxylic acids and alcohols in the presence of an amine base, the corresponding esters were formed rapidly at room temperature. Moreover, dehydrative condensation between carboxylic acids and amines using ATD-DMAP proceeded in high yield.
Chemoselective Amide-Forming Ligation Between Acylsilanes and Hydroxylamines Under Aqueous Conditions
Deng, Xingwang,Zhou, Guan,Tian, Jing,Srinivasan, Rajavel
, p. 7024 - 7029 (2020/12/29)
We report the facile amide-forming ligation of acylsilanes with hydroxylamines (ASHA ligation) under aqueous conditions. The ligation is fast, chemoselective, mild, high-yielding and displays excellent functional-group tolerance. Late-stage modifications of an array of marketed drugs, peptides, natural products, and biologically active compounds showcase the robustness and functional-group tolerance of the reaction. The key to the success of the reaction could be the possible formation of the strong Si?O bond via a Brook-type rearrangement. Given its simplicity and efficiency, this ligation has the potential to unfold new applications in the areas of medicinal chemistry and chemical biology.
Volatiles from the Psychrotolerant Bacterium Chryseobacterium polytrichastri
Lauterbach, Lukas,Dickschat, Jeroen S.
, p. 3608 - 3617 (2020/09/22)
The flavobacterium Chryseobacterium polytrichastri was investigated for its volatile profile by use of a closed-loop stripping apparatus (CLSA) and subsequent GC-MS analysis. The analyses revealed a rich headspace extract with 71 identified compounds. Compound identification was based on a comparison to library mass spectra for known compounds and on a synthesis of authentic standards for unknowns. Important classes were phenylethyl amides and a series of corresponding imines and pyrroles.
Antagonism of quorum sensing phenotypes by analogs of the marine bacterial secondary metabolite 3-methyl-N-(20-phenylethyl)-butyramide
Meschwitz, Susan M.,Teasdale, Margaret E.,Mozzer, Ann,Martin, Nicole,Liu, Jiayuan,Forschner-Dancause, Stephanie,Rowley, David C.
, (2019/07/15)
Quorum sensing (QS) antagonists have been proposed as novel therapeutic agents to combat bacterial infections. We previously reported that the secondary metabolite 3-methyl-N-(20-phenylethyl)-butyramide, produced by a marine bacterium identifie
Stereodivergent Synthesis through Catalytic Asymmetric Reversed Hydroboration
Gao, Tao-Tao,Zhang, Wen-Wen,Sun, Xin,Lu, Hou-Xiang,Li, Bi-Jie
supporting information, p. 4670 - 4677 (2019/03/19)
The control of chemo-, regio-, diastereo-, and enantioselectivity is a central theme in organic synthesis. The capability to obtain the full set of stereoisomers of a molecule would significantly enhance the efficiency for the synthesis of natural product analogues and creation of chiral compound libraries for drug discovery. Despite the tremendous progress achieved in the field of asymmetric synthesis in the past decades, the precise control of both relative and absolute configurations in catalyst-controlled reactions that create multiple stereocenters remains a significant synthetic challenge. We report here the development of a catalyst-controlled hydroboration with hitherto unattainable selectivity. The Rh-catalyzed hydroboration of α, β-unsaturated carbonyl compounds with pinacolborane proceeds with high levels of regio-, diastereo-, and enantioselectivities to provide a hydroboration product with two vicinal stereocenters. Through the appropriate choice of substrate geometry (E or Z) and ligand enantiomer (S or R), all the possible diastereoisomers are readily accessible. The boron-containing products underwent many stereospecific transformations, thus providing a strategy for collective stereodivergent synthesis of diverse valuable chiral building blocks.
N-Acyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamides: Highly selective and efficient reagents for acylation of amines in water
Ebrahimi, Sara,Saiadi, Safoura,Dakhilpour, Simin,Mirsattari, Seyed Nezamoddin,Massah, Ahmad Reza
, p. 95 - 104 (2016/04/26)
A variety of N-acyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamides (1a-e) were synthesized in one pot from 4-chloroaniline under solvent-free conditions and have been developed as chemoselective N-acylation reagents. Selective protection of primary amines in the presence of secondary amines, acylation of aliphatic amines in the presence of aryl amines, and monofunctionalization of primary-secondary diamines as well as selective N-acylation of amino alcohols using these reagents are described. All of the acylation reactions were carried out in water as a green solvent. High stability and easy preparation of these acylating reagents are other advantages of this method.
CuCl/TBHP catalyzed synthesis of amides from aldehydes and amines in water
Lu, Shao-Yi,Badsara, Satpal Singh,Wu, Yi-Chun,Reddy, Daggula Mallikarjuna,Lee, Chin-Fa
supporting information, p. 633 - 636 (2016/01/26)
A CuCl/TBHP catalyzed amidation of aldehydes with amine under aqueous media is described. Both aliphatic and aromatic aldehydes coupled with a variety of amines under the reaction conditions employed.
2-Furanylboronic acid as an effective catalyst for the direct amidation of carboxylic acids at room temperature
Tam, Eric Kwok Wai,Rita,Liu, Lionel Yiqian,Chen, Anqi
, p. 1100 - 1107 (2015/02/19)
2-Furanylboronic acid has been identified as an inexpensive and effective catalyst for the dehydrative amide formation of carboxylic acids and amines. This transformation can be efficiently carried out at room temperature and is applicable to a wide range of carboxylic acids with primary and secondary amines to afford amides in good to excellent yields.
Tetraarylphosphonium-supported carbodiimide reagents: Synthesis, structure optimization and applications
Ginisty, Maryon,Roy, Marie-Noelle,Charette, Andre B.
, p. 2542 - 2547 (2008/09/19)
(Chemical Equation Presented) New tetraarylphosphonium (TAP)-supported alkyl- and arylcarbodiimides were synthesized and used as coupling reagents for esterification reactions, amidation reactions and dehydration reactions of hydroxyesters. Taking advantage of the solubility properties imparted by the tetraarylphosphonium unit, a simple precipitation and filtration allowed complete separation of the urea by-products. This paper describes the structure optimization study of the various TAP-supported carbodiimide reagents to obtain the desired reactivity and solubility profile. Furthermore, we have demonstrated that the diimide reagent can be regenerated from the urea to recycle the reagents.
