1341197-47-4Relevant academic research and scientific papers
Base-Promoted Aerobic Oxidation/Homolytic Aromatic Substitution Cascade toward the Synthesis of Phenanthridines
Maiti, Debabrata,Halder, Atreyee,De Sarkar, Suman
, p. 4941 - 4948 (2019/11/03)
The current protocol represents a transition metal-free synthesis of polysubstituted phenanthridines from abundant starting materials like benzhydrol and 2-iodoaniline derivatives. The reaction involves sequential oxidation of alcohol and direct condensation reaction with the amine resulting in a C?N bond formation followed by a radical C?C coupling in a cascade sequence. The used base potassium tert-butoxide plays a dual role in dehydrogenation and homolytic aromatic substitution reaction. Using this methodology, twenty substituted phenanthridine derivatives were synthesized with up to 85% isolated yield. (Figure presented.).
Coupling N-H Deprotonation, C-H Activation, and Oxidation: Metal-Free C(sp3)-H Aminations with Unprotected Anilines
Evoniuk, Christopher J.,Gomes, Gabriel Dos Passos,Hill, Sean P.,Fujita, Satoshi,Hanson, Kenneth,Alabugin, Igor V.
supporting information, p. 16210 - 16221 (2017/11/22)
An intramolecular oxidative C(sp3)-H amination from unprotected anilines and C(sp3)-H bonds readily occurs under mild conditions using t-BuOK, molecular oxygen and N,N-dimethylformamide (DMF). Success of this process, which requires mildly acidic N-H bonds and an activated C(sp3)-H bond (BDE 85 kcal/mol), stems from synergy between basic, radical, and oxidizing species working together to promote a coordinated sequence of deprotonation: H atom transfer and oxidation that forges a new C-N bond. This process is applicable for the synthesis of a wide variety of N-heterocycles, ranging from small molecules to extended aromatics without the need for transition metals or strong oxidants. Computational results reveal the mechanistic details and energy landscape for the sequence of individual steps that comprise this reaction cascade. The importance of base in this process stems from the much greater acidity of transition state and product for the 2c,3e C-N bond formation relative to the reactant. In this scenario, selective deprotonation provides the driving force for the process.
Double C-H amination by consecutive SET oxidations
Evoniuk, Christopher J.,Hill, Sean P.,Hanson, Kenneth,Alabugin, Igor V.
supporting information, p. 7138 - 7141 (2016/06/09)
A new method for intramolecular C-H oxidative amination is based on a FeCl3-mediated oxidative reaction of anilines with activated sp3 C-H bonds. The amino group plays multiple roles in the reaction cascade: (1) as the activating group in single-electron-transfer (SET) oxidation process, (2) as a directing group in benzylic/allylic C-H activation at a remote position, and (3) internal nucleophile trapping reactive intermediates formed from the C-H activation steps. These multielectron oxidation reactions proceed with catalytic amounts of Fe(iii) and inexpensive reagents.
PYRROLOQUINOLINE ALKALOIDS AS ANTIMALARIAL AGENTS AND PROCESS FOR THE PREPARATION THEREOF
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Page/Page column 19; 21; 23, (2013/08/28)
The patent provides novel compounds with potential anti-malarial activity and process of synthesis thereof. Further, the process for the synthesis of known antimalarial natural products marinoquinazolinone A-F, aplidiopsamine A and their potential antimal
Intramolecular direct C-H bond arylation from aryl chlorides: A transition-metal-free approach for facile access of phenanthridines
Wu, Yinuo,Wong, Shun Man,Chan, Tek Long,Kwong, Fuk Yee,Mao, Fei
, p. 5306 - 5309,4 (2012/12/12)
A C-H arylation with aryl chloride is made viable through a transition-metal-free approach. In the presence of a simple diol associating with KOt-Bu, various phenanthridine derivatives can be conveniently accessed. In particular, only 10 mol % of simple and inexpensive ethylene glycol is required for this protocol. These results represent the first general examples of aryl chloride/C-H coupling under transition-metal-free conditions.
Intramolecular direct C-H bond arylation from aryl chlorides: A transition-metal-free approach for facile access of phenanthridines
Wu, Yinuo,Wong, Shun Man,Mao, Fei,Chan, Tek Long,Kwong, Fuk Yee
, p. 5306 - 5309 (2013/01/15)
A C-H arylation with aryl chloride is made viable through a transition-metal-free approach. In the presence of a simple diol associating with KOt-Bu, various phenanthridine derivatives can be conveniently accessed. In particular, only 10 mol % of simple and inexpensive ethylene glycol is required for this protocol. These results represent the first general examples of aryl chloride/C-H coupling under transition-metal-free conditions.
Pd-catalyzed imine cyclization: Synthesis of antimalarial natural products aplidiopsamine A, marinoquinoline A, and their potential hybrid nclite-M1
Mahajan, Jyoti P.,Suryawanshi, Yogeshwar R.,Mhaske, Santosh B.
supporting information, p. 5804 - 5807 (2013/01/15)
Palladium-catalyzed cyclization of imines has been developed to construct the extremely rare 3H-pyrrolo[2,3-c]quinoline ring system for diversity oriented first total synthesis of antimalarial marine natural product Aplidiopsamine A as well as synthesis o
Palladium-catalyzed intramolecular C-H activation/C-C bond formation: A straightforward synthesis of phenanthridines
Peng, Jinsong,Chen, Tonghui,Chen, Chunxia,Li, Bin
experimental part, p. 9507 - 9513 (2011/12/22)
The palladium-catalyzed intramolecular C-H activation/C-C cross-coupling has been developed for a straightforward and efficient synthesis of phenanthridines. With Pd(OAc)2 (4 mol %) as the catalyst, PCy 3 (8 mol %) as the ligand, and
