- [Omim]Cl/FeCl3-catalyzed cross-dehydrogenative-coupling of 1,4-benzoxazinones with various indoles
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A novel C(sp3)–C(sp2) cross-dehydrogenative-coupling procedure was developed for the reaction of benzoxazin-2-ones with indole derivatives. Thus, ionic liquid-mediated coupling of 1,4-benzoxazinone derivatives with indoles were observed in which [Omim]Cl/FeCl3 acted as both the solvent and the catalyst. Under [Omim]Cl/FeCl3-TBHP conditions, derivatives of 1 coupled at room temperature with indoles bearing various substituents to give the target products in good yields and within 0.5–2?h time period. The procedure is relatively environmentally friendly and is applicable to several derivatives of both reactants to access the desired products.
- Sharifi, Ali,Moazami, Maryam,Abaee, M. Saeed,Mirzaei, Mojtaba
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p. 2471 - 2480
(2020/05/25)
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- Iron-catalyzed oxidative sp3 carbon-hydrogen bond functionalization of 3,4-dihydro-1,4-benzoxazin-2-ones
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A novel and efficient iron-catalyzed sp3 carbon-hydrogen bond functionalization of benzoxazinone derivatives has been developed. For the first time, benzoxazin-2-ones were used as substrates in an oxidative dehydrogenative coupling reaction. The experiments were performed under mild reaction conditions to construct alkyl-aryl C(sp3)-C(sp2) bonds. The application of this method to the gram-scale synthesis of natural product cephalandole A has been accomplished in a 3-step sequence. A plausible one electron oxidation involved mechanism is proposed.
- Huo, Congde,Dong, Jie,Su, Yingpeng,Tang, Jing,Chen, Fengjuan
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supporting information
p. 13341 - 13344
(2016/11/18)
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- A convenient synthesis of 3,4-dihydro-1,4-benzoxazin-2-ones
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3,4-Dihydro-1,4-benzoxazin-2-one was prepared for the first time by catalytic hydrogenation of 4-benzyl-3,4-dihydro-1,4-benzoxazin-2-one. A simple and efficient synthesis of 4-benzyl- and 4-alkyl-3,4-dihydro-1,4-benzoxazin-2-one derivatives from ethyl 2-(2-hydroxyphenylamino)acetate and aldehydes is described. Some considerations regarding the reactivity of 3,4-dihydro-1,4-benzoxazin-2-ones are given.
- Zidar, Nace,Kikelj, Danijel
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p. 5756 - 5761
(2008/09/21)
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