41231-01-0Relevant articles and documents
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
, 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.
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.
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.
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,
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.