2007
DOI: 10.1021/ol701792j
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Cascade Coupling/Cyclization Process to N-Substituted 1,3-Dihydrobenzimidazol-2-ones

Abstract: Assembly of N-substituted 1,3-dihydrobenzimidazol-2-ones is achieved starting from methyl o-haloarylcarbamates via a CuI/amino acid catalyzed coupling with amines and subsequent condensative cyclization. A number of functional groups are tolerated by these reaction conditions, including vinyl, nitro, carboxylate, amide, ester, ketone, and silyl ether groups.

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Cited by 90 publications
(29 citation statements)
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“…Buchwald and co-authors developed the preparation of indulines [19], 2-aryl-4-quinolones [20] and N-alkylbenzimidazoles [21]. The group of Ma described a cascade approach for the production of benzofurans [22], dihydrobenzimidazole-2-ones [23], benzimidazoles [24], isoquinolines [25], pyrrolo [1,2-a]quinoxaline [26], and indoles [27]. Intramolecular C-X bond formation has been established by Batey's group to synthesize benzoxazoles [28], benzothiazoles [29] and aminobenzimidazoles [30].…”
Section: Resultsmentioning
confidence: 99%
“…Buchwald and co-authors developed the preparation of indulines [19], 2-aryl-4-quinolones [20] and N-alkylbenzimidazoles [21]. The group of Ma described a cascade approach for the production of benzofurans [22], dihydrobenzimidazole-2-ones [23], benzimidazoles [24], isoquinolines [25], pyrrolo [1,2-a]quinoxaline [26], and indoles [27]. Intramolecular C-X bond formation has been established by Batey's group to synthesize benzoxazoles [28], benzothiazoles [29] and aminobenzimidazoles [30].…”
Section: Resultsmentioning
confidence: 99%
“…In 2017, Ma's group reported a method to synthesize N ‐substituted 1,3‐dihydrobenzimidazol‐2‐ones 40 via CuI/ L ‐proline‐catalyzed cascade coupling/cyclization of methyl o ‐haloarylcarbamates 38 and amines 39 (Scheme 8). [ 37 ] This method featured advantages of excellent functional groups and forming the products in good yields, but only aryl iodides could be applied in this reaction.…”
Section: L‐proline‐assisted Copper‐catalyzed Cascade Reactionsmentioning
confidence: 99%
“…It is important to note that benzimidazolone constitutes the core structure of numerous pharmaceuticals, agrochemicals, inhibitors, pigments, herbicides, and fine chemicals (Monforte et al., 2010, Palin et al., 2008, Mastalerz and Oppel, 2012, Mir et al., 2012, Nale and Bhanage, 2015). To date, although there are a number of approaches reported for the synthesis of such compounds, including the cyclization of o -phenylenediamine with phosgene or CO surrogates (Scheme 2, path a), (Monforte et al., 2009, Kuethe et al., 2004, Diao et al., 2009) the cyclization of o -haloanilines involving C–N bond formation (paths b and c) (Zou et al., 2007, An et al., 2016), the oxidative aryl C–H amidation of N-disubstituted ureas (path d) (Beyer et al., 2001, Li et al., 2008, Yu et al., 2015), PhIO-induced Hofmann rearrangement of amides followed by intramolecular nucleophilic attack by an ortho -amino group (path e) (Łukasik and Wróbel, 2016), and the addition of anilines to isocyanates followed by intramolecular oxidative C–H amidation (path f) (Youn and Kim, 2016, Allen and Tidwell, 2013), to the best of our knowledge, the direct construction of benzimidazolones incorporated with additional functionalities from easily available feedstocks is still lacking. On the basis of our new observation, we herein present, for the first time, a multicomponent synthesis of functional benzimidazolones via tandem C–H aminations and alkyl deconstructive carbofunctionalization.
Scheme 2Existing Main Approaches for the Synthesis of Benzimidazolones
…”
Section: Introductionmentioning
confidence: 99%