1514933-78-8Relevant articles and documents
Accessing Polysubstituted Quinazolines via Nickel Catalyzed Acceptorless Dehydrogenative Coupling
Parua, Seuli,Sikari, Rina,Sinha, Suman,Chakraborty, Gargi,Mondal, Rakesh,Paul, Nanda D.
, p. 11154 - 11166 (2018)
Two environmentally benign methods for the synthesis of quinazolines via acceptorless dehydrogenative coupling of 2-aminobenzylamine with benzyl alcohol (Path A) and 2-aminobenzylalcohol with benzonitrile (Path B), catalyzed by cheap, earth abundant and easy to prepare nickel catalysts, containing tetraaza macrocyclic ligands (tetramethyltetraaza[14]annulene (MeTAA) or 6,15-dimethyl-8,17-diphenyltetraaza[14]annulene (MePhTAA)) are reported. A wide variety of substituted quinazolines were synthesized in moderate to high yields starting from cheap and easily available starting precursors. A few control reactions were performed to understand the mechanism and to establish the acceptorless dehydrogenative nature of the catalytic reactions.
Laccase-Based Oxidative Catalytic Systems for the Aerobic Aromatization of Tetrahydroquinazolines and Related N-Heterocyclic Compounds under Mild Conditions
Saadati, Shaghayegh,Ghorashi, Nadya,Rostami, Amin,Kobarfard, Farzad
, p. 4050 - 4057 (2018/08/21)
In this work, for the first time, laccase (metalloenzyme)/3,5-di-tert-butylcatechol (DTBC) as a new class of bioinspired quinone-based cooperative catalytic oxidation system and laccase/2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) catalyst system were used for the aerobic oxidative synthesis of 2-substituted quinazolines through cascade reaction of structurally divers aldehydes with 2-aminobenzylamine. The products were obtained in good to high yields in phosphate buffer (0.1 m, 12.5 mL, pH = 4.5) and acetonitrile (4 vol.-%) mixture as solvent at 45 °C. Other N-heterocycles are also successfully oxidized to their aromatic counterparts.
Bioinspired aerobic oxidation of secondary amines and nitrogen heterocycles with a bifunctional quinone catalyst
Wendlandt, Alison E.,Stahl, Shannon S.
supporting information, p. 506 - 512 (2014/01/23)
Copper amine oxidases are a family of enzymes with quinone cofactors that oxidize primary amines to aldehydes. The native mechanism proceeds via an iminoquinone intermediate that promotes high selectivity for reactions with primary amines, thereby constraining the scope of potential biomimetic synthetic applications. Here we report a novel bioinspired quinone catalyst system consisting of 1,10-phenanthroline-5,6-dione/ZnI2 that bypasses these constraints via an abiological pathway involving a hemiaminal intermediate. Efficient aerobic dehydrogenation of non-native secondary amine substrates, including pharmaceutically relevant nitrogen heterocycles, is demonstrated. The ZnI2 cocatalyst activates the quinone toward amine oxidation and provides a source of iodide, which plays an important redox-mediator role to promote aerobic catalytic turnover. These findings provide a valuable foundation for broader development of aerobic oxidation reactions employing quinone-based catalysts.
