- Catalytic substitution/cyclization sequences of: O -substituted Isocyanates: Synthesis of 1-alkoxybenzimidazolones and 1-alkoxy-3,4-dihydroquinazolin-2(1 H)-ones
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O-Substituted isocyanates (O-isocyanates) have rarely been used in organic synthesis, given their tendency to undergo side reactions (e.g., trimerization). Herein, we show that masked (blocked) O-isocyanate precursors allow one-pot or cascade reaction sequences featuring base-catalyzed substitution with 2-iodoanilines and 2-iodobenzylamines followed by copper-catalyzed cyclization, to form benzimidazolones and 3,4-dihydroquinazolin-2(1H)-ones. This work shows that O-isocyanates can serve as efficient building blocks for the synthesis of hydroxylamine-containing heterocycles.
- Wang, Qiang,An, Jing,Alper, Howard,Xiao, Wen-Jing,Beauchemin, André M.
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p. 13055 - 13058
(2017/12/15)
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- Synthesis and SAR of 1-hydroxy-1 H -benzo[ d ]imidazol-2(3 H)-ones as inhibitors of d -amino acid oxidase
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A series of 1-hydroxy-1H-benzo[d]imidazol-2(3H)-ones were synthesized and evaluated for their ability to inhibit human and porcine forms of d-amino acid oxidase (DAAO). The inhibitory potency is largely dependent on the size and position of substituents o
- Berry, James F.,Rais, Rana,Slusher, Barbara S.,Tsukamoto, Takashi,Ferraris, Dana V.,Duvall, Bridget,Hin, Niyada,Alt, Jesse,Thomas, Ajit G.,Rojas, Camilo,Hashimoto, Kenji
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p. 839 - 843,5
(2020/09/15)
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