41231-01-0Relevant academic research and scientific papers
A direct, regioselective palladium-catalyzed synthesis of N-substituted benzimidazoles and imidazopyridines
Alonso, Jorge,Halland, Nis,Nazare, Marc,R'Kyek, Omar,Urmann, Matthias,Lindenschmidt, Andreas
supporting information; experimental part, p. 234 - 237 (2011/03/20)
Unsymmetric, N-substituted benzimidazoles and imidazopyridines can be prepared directly from 2-halonitroarenes and amides through Pd(TFA) 2/(R)-BINAP-catalyzed cross-coupling and subsequent reductive aminocyclization. This sequence can be conducted by a one-pot procedure. The method is versatile and allows the straightforward, regioselective preparation of these important nitrogen heterocycles. Unsymmetrical, N-substituted benzimidazoles can be prepared directly from 2-halonitroarenes and amides through Pd(TFA)2/(R)-BINAP-catalyzed cross-coupling and subsequent reductive aminocyclization.This sequence can be conducted by a one-pot procedure. The method is versatile and allows the straightforward, regioselective preparation of these important nitrogen heterocycles. Copyright
Reactivity-controlled regioselectivity: A regiospecific synthesis of 1,2-disubstituted benzimidazoles
Deng, Xiaohu,Mani, Neelakandha S.
experimental part, p. 680 - 686 (2010/03/04)
We demonstrate exceptional levels of regioselectivity in the tandem, animation reactions between 1,2-differentiated dihaloarenes and N-substituted amidines, The regiochemical outcome of this Cul-catalyzed reaction is achieved through a combination of N1/N2 chemoselectivity on the amidine and reactivity-controlled X1/X2 chemoselectivity on the 1,2-dihaloarene. This reaction proves to be fairly general for the regiospecific synthesis of 1,2-substituted benzimidazoles.
Metallic Compound and Organic Electroluminescence Device Comprising the Same
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Page/Page column 12, (2008/12/08)
The present invention relates to a light emitting transition metal compound represented by the Chemical Formula 1 and Chemical Formula 2 and an organic electroluminescence device including the same. In the above Chemical Formulae 1 and 2, M is Ir, Pt, Rh,
A REGIOSELECTIVE COPPER CATALYZED SYNTHESIS OF BENZIMIDAZOLES AND AZABENZIMIDAZOLES
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Page/Page column 37, (2009/03/07)
The present invention relates to a process for the regioselective synthesis of compounds of the formula (I), wherein R0; R1; R2; R3; R4; R5; A1; A2; A3; A4; Q and J have the meanings indicated in the claims. The present invention provides a direct copper catalyzed regioselective process to a wide variety of unsymmetrical, multifunctional N/-substituted benzimidazoles or azabenzimidazoles of formula I starting from 2-halo-nitroarenes and N/-substituted amides. The process is useful for the production of pharmaceuticals, diagnostic agents, liquid crystals, polymers, herbicides, fungicidals, nematicidals, parasiticides, insecticides, acaricides and arthropodicides.
A regioselective palladium catalyzed synthesis of benzimidazoles and azabenzimidazoles
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Page/Page column 22, (2008/06/13)
The present invention relates to a process for the regioselective synthesis of compounds of the formula I, wherein R0; R1; R2; R3; R4; R5; A1; A2; A3; A4, Q and J have the meanings indicated in the claims. The present invention provides a direct palladium catalyzed, regioselective process to a wide variety of unsymmetrical, multifunctional N-substituted benzimidazoles or azabenzimidazoles of formula I starting from 2-halo-nitroarenes and N-substituted amides useful for the production of pharmaceuticals, diagnostic agents, liquid crystals, polymers, herbicides, fungicidals, nematicidals, parasiticides, insecticides, acaricitdes and arthropodicides.
New Synthesis of 11-Acyl-5,11-dihydro-6H-pyridobenzodiazepin-6-ones and Related Studies
Kovac, T.,Oklobdzija, M.,Comisso, G.,Decorte, E.,Fajdiga, T.,et al.
, p. 1339 - 1349 (2007/10/02)
New synthesis of 11-acyl-5,11-dihydro-6H-pyridobenzodiazepin-6-ones (42-44) is reported.The crucial steps (Scheme VI) represented N-oxidation of 1 (1A) to 35 (35A), facilitated ring-closure of 36 into 37, its subsequent N-α-chloroacetylation to 38, aminolysis to 39-41 (involving N-O anchimeric assistance as depicted in 38A) and deoxygenation to 42-44 (Scheme VII).The central intermediate 37 is also obtained on oxygenation of 2, a new synthesis of which was reported in the previous paper of this series .Other attempts of cyclisation "from the top" or "from the bottom" (Scheme I) are described.Thus, interaction of 1 with acetamide afforded 3 and 4 instead of the expected 2A.Compound 5 cyclised into 3-pyridoquinazolone 6 while its 2-(4'-methylpiperazin-1'-yl) analogue 9 was observed to be unstable for the attempted ring-opening and reclosure to 42. "From the bottom" cyclisations of 10A-10C, via intermediary amines 11A-11C failed and pyridoquinazolinone 13 was isolated (Scheme V).The attempted oxidative cyclisation of the compounds 15 and 18 into 2 and 42, respectively, 13 afforded imidazolopyridine derivative (18-19), while 15 remained unchanged. 3-Acylamino-2-arylaminopyridines (21-24), cyclised into the imidazolopyridines 29-30.Model compounds 45-50 were prepared to study selective aminolysis of the chlorine atoms in 2-chloro-3-(2'-chlorobenzoyl)aminopyridine 1, and its N-oxide 35.
