155885-65-7Relevant articles and documents
Access to 1-indolyltetrahydro-β-carbolines: via metal-free cross-dehydrogenative coupling: The total synthesis of eudistomin U, isoeudistomin U and 19-bromoisoeudistomin U
Ranjani, Ganapathy,Nagarajan, Rajagopal
, p. 757 - 760 (2021/02/03)
A highly selective and captivating metal-free cross-dehydrogenative coupling for the cross-coupling of two reactive nucleophiles such as tetrahydro-β-carboline and indoles is developed. A series of 1-indolyltetrahydro-β-carboline derivatives were synthesized in excellent to moderate yields. Temperature, time and concentration control resulted in mono indolylation selectively. Moreover, the total synthesis of eudistomin U and isoeudistomin U and the first total synthesis of 19-bromoisoeudistomin U were accomplished.
Bioinspired aerobic oxidation of secondary amines and nitrogen heterocycles with a bifunctional quinone catalyst
Wendlandt, Alison E.,Stahl, Shannon S.
, 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.
