喹啉-4-胺的杂环到杂环合成路线：3-(2-硝基苯基)异恶唑的还原杂环化反应
Heterocycle-to-Heterocycle Route to Quinoline-4-amines: Reductive Heterocyclization of 3-(2-Nitrophenyl)isoxazoles.
作者信息
Coffman Keith C, Duong Vy, Bagdasarian Alex L, Fettinger James C, Haddadin Makhlouf J, Kurth Mark J
机构信息
Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616, http://chemistry.ucdavis.edu/faculty/department_faculty/mark_kurth.html.
Department of Chemistry, Department American University of Beirut, Institution, Beirut, Lebanon.
出版信息
European J Org Chem. 2014 Dec;2014(34):7651-7657. doi: 10.1002/ejoc.201403065.
Abstract
A variety of quinoline-4-amines were synthesized from substituted 3-(2-nitrophenyl)isoxazoles utilizing Zn or Fe dust and HOAc via a reductive heterocyclization process. The starting isoxazoles were synthesized from readily available starting materials. A brief survey of functional groups tolerated in this reductive heterocyclization was performed and several 10-amino-3,4-dihydrobenzo[b][1,6]naphthyridin-1(2H)-one and 9-amino-3,4-dihydroacridin-1(2H)-one examples were synthesized.
摘要
通过还原杂环化过程，利用锌粉或铁粉以及醋酸，从取代的3-(2-硝基苯基)异恶唑合成了多种喹啉-4-胺。起始异恶唑由易得的原料合成。对该还原杂环化过程中可耐受的官能团进行了简要研究，并合成了几个10-氨基-3,4-二氢苯并[b][1,6]萘啶-1(2H)-酮和9-氨基-3,4-二氢吖啶-1(2H)-酮的实例。
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