2016
DOI: 10.1039/c6ra06828f
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Synthesis of benzoimidazoquinazolines by cobalt-catalyzed isocyanide insertion–cyclization

Abstract: An efficient and practical protocol for the synthesis of benzoimidazoquinazoline amines in moderate to good yields by the reaction of isocyanides and benzo[d]imidazol-anilines via a cobalt-catalyzed isocyanide insertion cyclization reaction into the two N-H active bonds is reported.

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Cited by 30 publications
(11 citation statements)
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“…Inexpensive K 2 S 2 O 8 is the preferred oxidant in these reactions.The cobalt-catalyzed insertion of isocyanides into 2-(2-aminoaryl)benzimidazoles 124 (Scheme 32 a) affords benzimidazole-fused 2-aminoquinazolines 125. [61] Ap lausible mechanism proceeds via the intermediate amidinoyl cobalt-(II) species 126, which undergoes asingle-electron oxidation, initiating the reductive elimination. Further one-electron oxidation of the liberated Co I species regenerates the active catalyst.…”
Section: Angewandte Chemiementioning
confidence: 99%
“…Inexpensive K 2 S 2 O 8 is the preferred oxidant in these reactions.The cobalt-catalyzed insertion of isocyanides into 2-(2-aminoaryl)benzimidazoles 124 (Scheme 32 a) affords benzimidazole-fused 2-aminoquinazolines 125. [61] Ap lausible mechanism proceeds via the intermediate amidinoyl cobalt-(II) species 126, which undergoes asingle-electron oxidation, initiating the reductive elimination. Further one-electron oxidation of the liberated Co I species regenerates the active catalyst.…”
Section: Angewandte Chemiementioning
confidence: 99%
“…Inexpensive K 2 S 2 O 8 is the preferred oxidant in these reactions. The cobalt‐catalyzed insertion of isocyanides into 2‐(2‐aminoaryl)benzimidazoles 124 (Scheme a) affords benzimidazole‐fused 2‐aminoquinazolines 125 . A plausible mechanism proceeds via the intermediate amidinoyl cobalt(II) species 126, which undergoes a single‐electron oxidation, initiating the reductive elimination.…”
Section: Insertions Of Isocyanides Into Heteroatom–metal Bondsmentioning
confidence: 99%
“…Isocyanides represent an important class of organic molecules which have a broad range of applications in biomedical chemistry and materials science owing to their diverse variations . In the past decades, transition-metal-catalyzed multicomponent reactions (MCRs) involving isocyanides have attracted great attention as a powerful tool in organic synthesis . Most of these strategies involved the formation of aryl- or alkenyl-palladium species and sequential coupling with different nucleophiles to afford various heterocycle compounds (Scheme a). , Although much progress has been achieved in this area, the exploration of different nucleophilic partners to trap the active Pd intermediates should be very important.…”
mentioning
confidence: 99%