56031-19-7Relevant academic research and scientific papers
Palladium-Catalyzed, N-(2-Aminophenyl)acetamide-Assisted Ortho-Arylation of Substituted Benzamides: Application to the Synthesis of Urolithins B, M6, and M7
Reddy, M. Damoder,Blanton, Alexandra N.,Watkins, E. Blake
, p. 5080 - 5095 (2017)
Pd-catalyzed, selective, monoarylation of ortho-C-H bonds of various benzamides with aryl/heteroaryl iodides has been realized using N-(2-aminophenyl)acetamide (APA) as a new bidentate directing group for the first time. The reaction was tolerant of a wid
Towards a Sequential One-Pot Preparation of 1,2,3-Benzotriazin-4(3H)-ones Employing a Key Cp*Co(III)-catalyzed C?H Amidation Step
Chirila, Paula G.,Skibinski, Lauren,Miller, Keith,Hamilton, Alex,Whiteoak, Christopher J.
, p. 2324 - 2332 (2018/04/30)
1,2,3-benzotriazin-4(3H)-one derivatives have been recognised for their potential application as pesticides and pharmaceuticals and new methodologies for their preparation, starting from readily accessible reagents would therefore be an attractive proposition. A wide range of differently substituted benzamides are readily available, which provide an excellent substrate scaffold for the application of direct C?H functionalization protocols. In this context, herein we report the use of a Cp*Co(III) catalyst for the amidation of these benzamides, using 1,4,2-dioxazol-5-ones as amidating agent. The isolable intermediate 2-acetamido benzamide products can thereafter be converted to the desired 1,2,3-benzotriazin-4(3H)-one derivatives through the use of tert-butyl nitrite under mild conditions. It was found to be possible to perform the second step with the crude reaction mixture obtained from the initial C?H amidation step, leading to the overall development of a facile one-pot procedure for the preparation of a range of substituted 1,2,3-benzotriazin-4(3H)-one derivatives, requiring only 5 hours of reaction time, which is also applicable on a gram scale. In addition, the key Cp*Co(III)-catalyzed C?H amidation step has been studied by DFT calculations in order to fully elucidate the mechanism. (Figure presented.).
Iterative C?H Functionalization Leading to Multiple Amidations of Anilides
Park, Juhyeon,Lee, Jia,Chang, Sukbok
, p. 4256 - 4260 (2017/04/04)
Polyaminobenzenes were synthesized by the ruthenium-catalyzed iterative C?H amidation of anilides using dioxazolones as an amino source. This strategy could be implemented by the sequential activation of C?H bonds of formerly generated compounds by cascade chelation assistance of newly installed amide groups. Computational studies provided a rationale.
Novel Synthesis and Rearrangement of 3,1,5-Benzoxadiazepines
Mazurkiewicz, Roman
, p. 1279 - 1288 (2007/10/02)
N,N'-Diacyl-o-phenylenediamines react with dibromotriphenylphosphorane in the presence of triethylamine as HBr captor to give 3,1,5-benzoxadiazepines in good yields.If the reaction is carried out without acid acceptor the initially formed 3,1,5-benzoxadia
