105174-48-9Relevant articles and documents
Investigation of dopamine analogues: Synthesis, mechanistic understanding, and structure-property relationship
Hu, Huamin,Dyke, Jason Christopher,Bowman, Brett Allen,Ko, Ching-Chang,You, Wei
, p. 9873 - 9882 (2016)
Dopamine, perhaps the simplest molecule that covalently links catechol and amine, together with its derivatives, has shown impressive adhesive and coating properties with its polymers. However, the scope of the molecules is rather limited, and the polymer
Intramolecular Cyclization of Brominated Oxime Ether Promoted with Ytterbium(0) to the Synthesis of Cyclic Imines
Wang, Yiqiong,Huang, Fei,Zhang, Songlin
supporting information, p. 5178 - 5181 (2020/08/13)
The first utility of ytterbium(0) as a mediating-metal in the intramolecular cyclization of brominated oxime ether was reported in this paper. In contrast to the prior methods, the N–O bond was used as a receptor of nucleophilic reagent, rather than as a source of N-centered radicals. Cyclic imines were obtained in this one-pot reaction with a broad scope of substrates and feasible reaction conditions.
Iminyl Radicals by Reductive Cleavage of N-O Bond in Oxime Ether Promoted by SmI2: A Straightforward Synthesis of Five-Membered Cyclic Imines
Huang, Fei,Zhang, Songlin
supporting information, p. 7430 - 7434 (2019/10/11)
A new generation method of N-centered radicals from the reductive cleavage of the N-O bond in oxime ether promoted by SmI2 is reported for the first time. The in-situ-generated N-centered radicals underwent intramolecular cyclization to afford five-membered cyclic imines in two manners: N-centered radical addition and N-centered anion nucleophilic substitution. From a synthetic point of view, an efficient synthetic method of five-membered cyclic imines was developed. A mechanism of the transformation was proposed.
Efficient, one-pot, BF3·OEt2-mediated synthesis of substituted N-aryl lactams
Chaturvedi, Devdutt,Chaturvedi, Amit K.,Mishra, Nisha,Mishra, Virendra
, p. 2627 - 2630,4 (2012/12/12)
A quick, efficient, one-pot, BF3·OEt2-mediated synthesis of substituted N-aryl lactams in good to excellent yields by reaction of various substituted arenes with a variety of ω-azido alkanoic acid chlorides at room temperature is reported.
An efficient and novel approach for the synthesis of substituted N-aryl lactams
Chaturvedi, Devdutt,Chaturvedi, Amit K.,Mishra, Nisha,Mishra, Virendra
, p. 9148 - 9151,4 (2012/12/12)
A quick, efficient, one-pot method for the synthesis of substituted N-aryl lactams through the reaction of various kinds of corresponding substituted arenes with a variety of ω-azido alkanoic acid chlorides using a Lewis acid (i.e. EtAlCl2) at room temperature, through the in situ involvement of a Friedel-Crafts reaction followed by intramolecular Schimdt rearrangement was developed, and afforded good to excellent yields.
Synthesis of sialic acids via desymmetrization by ring-closing metathesis.
Voight, Eric A,Rein, Christian,Burke, Steven D
, p. 8489 - 8499 (2007/10/03)
Formal total syntheses of the naturally occurring deaminated sialic acids KDN (2), a potential oncofetal antigen, and N-acetylneuraminic acid (Neu5Ac, 1), the most naturally abundant sialic acid, have been accomplished in 46% and 9.3% overall yield, respectively, via a novel ketalization/ring-closing metathesis sequence. The rapid introduction of all oxygen and nitrogen functionality in a completely stereocontrolled manner exploited a rigid 6,8-dioxabicyclo[3.2.1]oct-2-ene template. The 2,7-anhydro-KDN derivative 40 served as an advanced intermediate in each of the two syntheses.
Formal synthesis of (+)-3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) via desymmetrization by ring-closing metathesis
Burke, Steven D.,Voight, Eric A.
, p. 237 - 240 (2007/10/03)
equation presented Formal synthesis of the naturally occurring deaminated sialic acid KDN, a potential oncofetal antigen, has been accomplished in 45% overall yield via a novel ketalization/ring-closing metathesis sequence. The rapid introduction of all o
Synthesis of Phenolic Ketones, an Ester Ketone of Guaiacol, and a Ketone of Veratrole Containing Chlorine, Bromine, or Iodine in the Side-chain
Kossmehl, Gerhard,Frohberg, Hans-Christian
, p. 50 - 64 (2007/10/02)
The ω-bromo and ω-chloro ketones 1-8, 10-14 of phenols as well as the ω-bromo ketone 9 of veratrole are synthesized according to the Friedel-Crafts acylation (FCA) using different variations and specific reaction conditions.Under these conditions hydroquinone furnishes the esters of the ω-bromo- and ω-chlorocarboxylic acids 28-31, whereas phloroglucinol does not result in defined reaction products.Guaiacol yields 16 with an ester as well as a ketone group at its aromatic nucleus.Bromination of 3',4'-dihydroxyisobutyrophenone with CuBr2 leads to 2-bromo-3',4'-dihydroxyisobutyrophenone (15).The ω-iodo ketones 17-27 of phenols and their methyl ethers have been obtained from the corresponding ω-bromo or ω-chloro ketone on treatment with NaI in acetone.
