2013
DOI: 10.1021/jo302471z
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Nucleophilic Addition of Benzimidazoles to Alkynyl Bromides/Palladium-Catalyzed Intramolecular C–H Vinylation: Synthesis of Benzo[4,5]imidazo[2,1-a]isoquinolines

Abstract: An efficient "one-pot" route for the synthesis of benzo[4,5]imidazo[2,1-a] isoquinolines has been developed via nucleophilic addition of 2-aryl benzimidazoles to alkynyl bromides and subsequent palladium-catalyzed intramolecular C-H vinylation.

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Cited by 58 publications
(24 citation statements)
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“…In light of these results and based on literature precedence,19, 21, 22, 25 we considered two possible reaction pathways (Scheme ); either a base‐mediated addition of the amidine to the bromoacetylene took place, affording intermediates 4 and 4′ , which, upon cyclization, led to the observed imidazole 3 (path A), or, alternatively, bromoacetylene 2 hydrolyzed affording a highly reactive 2‐bromoketone 5 , which, by reacting with the amidine, resulted in the formation of the isolated product 3 (path B). This pathway would easily explain the experimentally observed important role of water needed to achieve a high product yield.…”
Section: Methodsmentioning
confidence: 71%
See 1 more Smart Citation
“…In light of these results and based on literature precedence,19, 21, 22, 25 we considered two possible reaction pathways (Scheme ); either a base‐mediated addition of the amidine to the bromoacetylene took place, affording intermediates 4 and 4′ , which, upon cyclization, led to the observed imidazole 3 (path A), or, alternatively, bromoacetylene 2 hydrolyzed affording a highly reactive 2‐bromoketone 5 , which, by reacting with the amidine, resulted in the formation of the isolated product 3 (path B). This pathway would easily explain the experimentally observed important role of water needed to achieve a high product yield.…”
Section: Methodsmentioning
confidence: 71%
“…Also of interest was the multicomponent metal‐free synthesis of imidazoles reported by Wang and co‐workers,19 as it started from alkynes that were suggested to be oxidized to diketone,s which subsequently reacted with in situ‐formed amidines 20. In light of these results and considering our previous work,21 as well as findings by Li and co‐workers,22 we wondered about an alternative transition metal‐free approach and hypothesized that imidazole derivatives 3 could also result from base‐mediated reactions starting from easy‐to‐handle amidine hydrochlorides 1 and bromoacetylenes 2 (Scheme c). The realization of this idea is reported herein.…”
Section: Methodsmentioning
confidence: 73%
“…(Z)-1-(1-苯基-2-溴乙烯基)-2-苯基苯并咪唑(1b) [14] : 141.5, 138.7, 131.2, 130.9, 130.8, 129.6, 128.9, 128.8, 128.2, 127.7, 126.7, 123.3, 123.1, 115.5, 115.3, 80.7 161.6, 152.9, 142.2, 136.6, 132.3, 131.5, 130.9, 130.3, 128.7, 128.6, 124.3, 124.0, 121.8, 121.5, 119.9, 114.1, 110.9, 78.1, 75.4, 55.4 149.5, 135.8, 133.1, 129.8, 129.6, 129.5, 129.3, 128.9, 128.8, 128.5, 128.0, 126.6, 123.9, 121.6, 83.9, 69.5 7, 142.2, 136.6, 135.4, 132.8, 130.8, 129.6, 129.5, 128.9, 128.8, 128.6, 126.7, 124.6, 121.9, 120.4, 111.3, 82.5, 72. 151.6, 142.1, 137.0, 136.6, 135.5, 132.8, 130.1, 129.8, 129.6, 128.9, 127.3, 126.7, 124.8, 124.7, 121.7, 120.4, 111.3, 82.2, 73 7, 142.5, 136.5, 132.7, 132.5, 131.6, 131.4, 129.5, 129.2, 129.0, 128.7, 128.3, 125.1, 124.8, 121.3, 120.6, 111.6, 77.8, 75.9, 56. 7, 153.1, 142.2, 141.1, 136.6, 133.5, 129.4, 128.6, 126.1, 124.4, 124.2, 120.2, 117.8, 116.0, 115.9, 111.0, 77.7, 74.4, 21.6 MHz) δ: 143.9, 141.8, 134.7, 124.4, 123.6, 120.5, 110.8, 73.6, 68.0, 31.2, 28.5, 28.5, 22.4, 18.3, 14. 7, 142.8, 133.2, 131.8, 129.8, 129.2, 128.6, 125.4, 121.1, 120.8, 111.7, 75.9, 73 2, 140.4, 133.2, 131.9, 130.8, 129.3, 128.6, 125.0, 121.7, 120.8, 111.2, 75.6, 74.1.…”
Section: 产物表征分析mentioning
confidence: 99%
“…在此, 论文拟通过碱促进的咪唑衍 生物与炔基溴直接脱溴化氢来合成芳香炔胺化合物 [13] , 如图 2 所示. [14,15] , 实验研究也证实 1b 的形成并不是通过主产物 [11,17] , 近年研究 也表明, 偶联反应的发生可能是体系中(如碱、配体或溶 剂)所含痕量过渡金属在起催化作用 [17] . 为此, 我们对 2, 128.9, 128.6, 128.5, 128.2, 124.7, 124.6, 120.7, 120.0, 111.2, 77.4, 75.3.…”
unclassified
“…[11] Later, Peng described sequential nucleophilic addition and Pd catalyzed intramolecular CÀH vinylation of 2-aryl benzimidazole with alkynyl bromide. [12] Villar also reported the Rh(III) catalyzed double-oxidative annulation of 2-arylbenzimidazoles with alkynes. [13] Our interest in transition metal catalyzed reaction, [14] and construction of pharmacological important benzimidazoles [15] motivated us to explore the Ru-catalyzed ortho selective CÀH activation/NÀH annulation of 2arylbenzimidazole 1 with various substituted styrene 2 for the synthesis of dihydrobenzoimidazo[2,1-a]isoquinolines (Scheme 1).…”
Section: Introductionmentioning
confidence: 99%