99514-85-9Relevant academic research and scientific papers
Iridium-catalyzed intramolecular C–N and C–O/S cross-coupling reactions: Preparation of benzoazole derivatives
Shi, Yajie,Zhou, Qifan,Du, Fangyu,Fu, Yang,Du, Yang,Fang, Ting,Chen, Guoliang
supporting information, (2019/09/10)
The irdium-catalyzed intramolecular arylcarbon-hetero cross-coupling reactions with o-haloarylamides or o-haloarylamidine have been effectively achieved using KOAc and just 1 mol% catalyst. The [Ir(cod)Cl]2 was proved to be more potential for smoothly assembling functional structures benzimidazoles, benzoxazoles and benzothiazoles, which was superior to Cu- and Pd-catalyzed systems. Simultaneously, a concise and efficient synthesis of tafamidis was developed in 5-g scale.
A comparative study of the catalytic activity of Co- and CoFe2O4-NPs in C-N and C-O bond formation: synthesis of benzimidazoles and benzoxazoles from o-haloanilides
Hajipour, Abdol R.,Khorsandi, Zahra
, p. 10474 - 10481 (2016/12/07)
Nanoparticles of cobalt ferrite (CoFe2O4-NPs) and pure cobalt (Co-NPs) were synthesized, and after characterization, their catalytic activities for dehalogenative intramolecular C-O and C-N bond formation reactions were investigated and compared. These inexpensive and efficient catalysts enabled creation of new methods for the synthesis of benzimidazoles and benzoxazoles in green media, with ligand-free and mild reaction conditions. All the reactions resulted in moderate to excellent yields under the optimized reaction conditions; however, the reactions using Co-NPs as the catalyst were completed in relatively shorter reaction times. Furthermore, analysis showed that the reusability of the two catalytic systems is approximately comparable.
Green, efficient and large-scale synthesis of benzimidazoles, benzoxazoles and benzothiazoles derivatives using ligand-free cobalt-nanoparticles: As potential anti-estrogen breast cancer agents, and study of their interactions with estrogen receptor by mo
Hajipour, Abdol R.,Khorsandi, Zahra,Mortazavi, Maryam,Farrokhpour, Hossein
, p. 107822 - 107828 (2016/01/09)
A facile and high yielding method for the synthesis of 2-aryl benzoxazoles, benzimidazole and benzothiazoles is reported employing cobalt oxide nanoparticles. The cobalt oxide nanoparticles were used as a convenient, green, easy available and highly effic
Pd(OAc)2-catalyzed carbonylative coupling of aryl iodide with ortho-haloamines in water
Tambade, Pawan J.,Patil, Yogesh P.,Qureshi, Ziyauddin S.,Dhake, Kishor P.,Bhanage, Bhalchandra M.
supporting information; experimental part, p. 176 - 185 (2011/10/31)
The carbonylative cross coupling of aryl iodide with ortho-haloaniline to ortho-haloanilide using phosphine-free Pd(OAc)2 catalyst in water as a reaction medium has been studied. The present protocol facilitated the reaction of o-haloanilines with a wide variety of hindered and functionalized aryl iodides, affording good yields of the desired products. The protocol was also extended for the synthesis of benzoxazoles through cyclization of ortho-haloanilide using Cu(acac)2 catalyst. Taylor & Francis Group, LLC.
Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides
Evindar, Ghotas,Batey, Robert A.
, p. 1802 - 1808 (2007/10/03)
A general method for the formation of benzoxazoles via a copper-catalyzed cyclization of ortho-haloanilides is reported. This approach complements the more commonly used strategies for benzoxazole formation which require 2-aminophenols as substrates. The reaction involves an intramolecular C-O cross-coupling of the ortho-haloanilides and is believed to proceed via an oxidative insertion/reductive elimination pathway through a Cu(I)/Cu(III) manifold. The reaction is also applicable to the formation of benzothiazoles. A variety of ligands including 1,10-phenanthroline and N,N′- dimethylethylenediamine were shown to provide ligand acceleration/stabilization in the reaction. Optimal conditions for cyclization used a catalyst combination of CuI and 1,10-phenanthroline (10 mol %). The method was amenable to a parallel-synthesis approach, as demonstrated by the synthesis of a library of benzoxazoles and benzothiazoles substituted at various positions in the ring. Most examples utilized the cyclization of ortho-bromoanilides, but orthoiodoanilides and ortho-chloroanilides also undergo a reaction under these conditions. The rate of reaction of the ortho-haloanilides follows the order I > Br > Cl, consistent with oxidative addition being the rate-determining step.
