16140-89-9Relevant academic research and scientific papers
Oxidation of Nonactivated Anilines to Generate N-Aryl Nitrenoids
Deng, Tianning,Mazumdar, Wrickban,Ford, Russell L.,Jana, Navendu,Izar, Ragda,Wink, Donald J.,Driver, Tom G.
supporting information, p. 4456 - 4463 (2020/03/05)
A low-temperature, protecting-group-free oxidation of 2-substituted anilines has been developed to generate an electrophilic N-aryl nitrenoid intermediate that can engage in C-NAr bond formation to construct functionalized N-heterocycles. The exposure of 2-substituted anilines to PIFA and trifluoroacetic acid or 10 mol percent Sc(OTf)3 triggers nitrenoid formation, followed by productive and selective C-NAr and C-C bond formation to yield spirocyclic- or bicyclic 3H-indoles or benzazepinones. Our experiments demonstrate the breadth of these oxidative processes, uncover underlying fundamental elements that control selectivity, and demonstrate how the distinct reactivity patterns embedded in N-aryl nitrenoid reactive intermediates can enable access to functionalized 3H-indoles or benzazepinones.
Rh2(II)-Catalyzed Ring Expansion of Cyclobutanol-Substituted Aryl Azides to Access Medium-Sized N-Heterocycles
Mazumdar, Wrickban,Jana, Navendu,Thurman, Bryant T.,Wink, Donald J.,Driver, Tom G.
supporting information, p. 5031 - 5034 (2017/05/04)
A new reactivity pattern of Rh2(II)-N-arylnitrenes was discovered that facilitates the synthesis of medium-sized N-heterocycles from ortho-cyclobutanol-substituted aryl azides. The key ring-expansion step of the catalytic cycle is both chemosel
Electrophilic intramolecular cyclization of functional derivatives of unsaturated compounds: V. Cyclization of anilides of styrylacetic acids in polyphosphoric acid
Vas'Kevich,Vas'Kevich,Daniluk, I. Yu.,Vovk
, p. 1175 - 1181 (2013/10/01)
Anilides of styrylacetic acids at heating in polyphosphoric acid undergo an intramolecular cyclization giving 1,5-diarylpyrrolidin-2-ones, 5-aryl-1,3,4,5-tetrahydro-2H-benzazepin-2-ones, and 5-(3-fluorophenyl) dihydrofuran-2(3H)-one, where the ratio of th
TETRAHYDRO-1H-BENZAZEPINONES AND HEXAHYDROAZEPINONES AS SELECTIVE CHOLECYSTOKININ-B RECEPTOR ANTAGONISTS
-
, (2008/06/13)
This invention relates to compounds of formula (I) wherein R. sup.1, R. sup.2, R 3, R 4 and X are as defined in the application. These compounds are CCK-B receptor antagonists and are useful in the treatment and prevention of central nervous system and gastrointestinal disorders. STR1
Regiochemistry of Radical Cyclisations (6-exo/7-endo and 7-exo/8-endo) of N-(o-Alkenylphenyl)-2,2-dichloroacetamides
Sato, Tatsunori,Ishida, Satoshi,Ishibashi, Hiroyuki,Ikeda, Masazumi
, p. 353 - 359 (2007/10/02)
N--2,2-dichloroacetamides, when treated with 2.2 mol-equiv. of Bu3SnH in the presence of a catalytic amount of azoisobutyronitrile, gave quinolin-2(1H)-one (6-exo closure) and/or 2H-1-benzazepin-2-one (7-endo closure) systems.In gene
