81316-49-6Relevant academic research and scientific papers
Visible light bromide catalysis for oxazoline, pyrrolidine, and dihydrooxazine synthesesviaCsp3-H functionalizations
Kaur, Navdeep,Ziegelmeyer, Elizabeth C.,Farinde, Olutayo N.,Truong, Jonathon T.,Huynh, Michelle M.,Li, Wei
supporting information, p. 10387 - 10390 (2021/10/14)
A catalytic benzylic Csp3-H functionalization protocol is described here. This visible light-mediated process is centered on the utilization of a bromide catalyst and oxidant to generate a nitrogen (N)-centered radical for a site-selective hydrogen atom transfer (HAT) process. This strategy enabled the unconventional syntheses of a number of N-heterocycles dependent on the amide identity. We also discovered a nucleophilicity-dependent kinetic resolution for stereochemical differentiation of Csp3-H bonds that enabled the stereoselective synthesis ofcis- andtrans-oxazolines.
Synthesis of 2,5-disubstituted oxazoles and oxazolines catalyzed by ruthenium(II) porphyrin and simple copper salts
Zhong, Chuan Long,Tang, Bo Yang,Yin, Ping,Chen, Yue,He, Ling
experimental part, p. 4271 - 4277 (2012/06/18)
A novel and moderate synthesis of 2,5-disubstituted oxazoles and oxazolines involving ruthenium(II) porphyrin-copper chloride catalyzed cyclization was developed. These reactions using readily available benzene carboxylic acids and phenylethenes or phenylacetylenes are performed under mild conditions. The reactions proceed in series, giving rise to the formation of an intermolecular C-N bond and an intramolecular C-O bond, which yield oxazole or oxazoline derivatives simultaneously.
Oxazolines. 2. 2-Substituted 2-Oxazolines as Synthons for N-(β-Hydroxyethyl)arylalkylamines, Intermediates in a Synthesis of 1,2,3,4-Tetrahydroisoquinolines and 2,3,4,5-Tetrahydro-1H-3-Benzazepines
Pridgen, Lendon N.,Killmer, Lewis B.,Webb, R. Lee
, p. 1985 - 1989 (2007/10/02)
2-(Arylalkyl)-2-oxazolines 4 (n = 1) and 2-aryl-2-oxazolines 4 (n = 0), the latter prepared in a novel reaction by cross-coupling aryl Grignard reagents with 2-(methylthio)-5-phenyl-2-oxazoline (10) and using palladium(II) chloride (14) as a catalyst, were reduced in a previously unreported reaction by diborane in refluxing THF to yield N-(β- hyroxyethyl)arylalkylamines 5 (n = 1,2).Amino alcohols 5 were cyclized to their respective heterocyclic derivatives 6 (n = 1,2) by treatment with H2SO4/TFA in refluxing methylene chloride.This paper disscuses how 2-substituted 2-oxazolines may be used to prepare1,2,3,4-tetrahydroisoquinolines 6 (n = 1) and 2,3,4,5-tetrahydro-1H-3-benzazepines 6 (n = 2) via amino alcohols 5.
