PhI(OCOCF3)(2)-Mediated Cyclization of o-(1-Alkynyl)benzamides: Metal-Free Synthesis of 3-Hydroxy-2,3-dihydroisoquinoline-1,4-dione

Yang Chao; Zhang Xiang; Zhang-Negrerie Daisy; Du Yunfei; Zhao Kang

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PhI(OCOCF3)(2)-Mediated Cyclization of o-(1-Alkynyl)benzamides: Metal-Free Synthesis of 3-Hydroxy-2,3-dihydroisoquinoline-1,4-dione

机译：PhI（OCOCF3）（2）介导的邻-（1-炔基）苯甲酰胺的环化反应：3-羟基-2,3-二氢异喹啉-1,4-二酮的无金属合成

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The synthesis of an undocumented skeleton of 3-hydroxy-2,3-dihydroisoquinoline-1,4-diones has been discovered and reported. The reaction consists of an intramolecular cyclization of o-(1-alkynyl)benzamides in MeCN/H2O, mediated by metal-free, hypervalent reagent of PhI(OCOCF3)(2), followed by an oxidative hydroxylation reaction: The mechanism consisting of two pathways has been proposed and discussed:

机译：已经发现并报道了3-羟基-2，3-二氢异喹啉-1，4-二酮的无证骨架的合成。该反应由邻位（1-炔基）苯甲酰胺在MeCN / H2O中的分子内环化，由无金属，高价的PhI（OCOCF3）（2）介导，然后进行氧化性羟基化反应：该机理由两个已经提出并讨论了以下途径：

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《The Journal of Organic Chemistry》 |2015年第10期|共9页
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Yang Chao; Zhang Xiang; Zhang-Negrerie Daisy; Du Yunfei; Zhao Kang;
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1. PhI(OCOCF3)(2)-Mediated Cyclization of o-(1-Alkynyl)benzamides: Metal-Free Synthesis of 3-Hydroxy-2,3-dihydroisoquinoline-1,4-dione [J] . Yang Chao, Zhang Xiang, Zhang-Negrerie Daisy, The Journal of Organic Chemistry . 2015,第10期

机译：PhI（OCOCF3）（2）介导的邻-（1-炔基）苯甲酰胺的环化反应：3-羟基-2,3-二氢异喹啉-1,4-二酮的无金属合成
2. Facile synthesis of sulfenyl-substituted isocoumarins, heterocycle-fused pyrones and 3-(inden-1-ylidene)isobenzofuranones by FeCl _3-promoted regioselective annulation of o-(1-alkynyl)benzoates and o-(1-alkynyl) heterocyclic carboxylates with disulfides [J] . Li Z., Hong J., Weng L., Tetrahedron . 2012,第5期

机译：FeCl _3-促进邻-（1-炔基）苯甲酸酯和邻-（1-炔基）杂环羧酸酯的区域选择性环化反应，可轻松合成亚磺酰基取代的异香豆素，杂环稠合的吡喃酮和3-（茚-1-基）异苯并呋喃酮二硫化物
3. p-Toluenesulfonic acid-mediated cyclization of o-(1-alkynyl)anisoles or thioanisoles: synthesis of 2-arylsubstituted benzofurans and benzothiophenes [J] . Maud Jacubert, Abdallah Hamze, Olivier Provot Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2009,第26期

机译：对甲苯磺酸介导的邻-（1-炔基）茴香醚或硫代苯甲醚的环化反应：2-芳基取代的苯并呋喃和苯并噻吩的合成
4. Synthesis of Nitrogen Heterocycles by Electrochemical Radical Cyclization Using an Arene Mediator [C] . Nobuhito Kurono, Fumikazu Komatsu, Eiichi Honda, The Meeting of the Electrochemical Society . 2003

机译：芳烃介体通过电化学自由基环化合成氮杂环
5. New developments toward the synthesis of heterocycles and applications in green chemistry. I. A simple and essentially one-pot synthesis of N-aminated heterocycles using phase transfer catalyst (Aliquat-336). II. Synthesis of pharmaceutically important pyrrole derivatives. III. Applications in green chemistry: Surfactant-mediated environmentally friendly cleavage of aromatic esters and trans-esterification under solvent-free neutral conditions . [D] . Patel, Nitinchandra. 2005

机译：杂环合成的新进展及其在绿色化学中的应用。 I.使用相转移催化剂（Aliquat-336）简单且基本上一锅合成N-胺化的杂环。二。药学上重要的吡咯衍生物的合成。三，在绿色化学中的应用：在无溶剂的中性条件下，表面活性剂介导的环境友好的芳族酯裂解和酯交换反应。
6. A Regio- and Stereoselective Synthesis of Cyclic Imidates via Electrophilic Cyclization of 2-(1-Alkynyl)benzamides. A Correction [O] . Saurabh Mehta, Tuanli Yao, Richard C. Larock -1

机译：阿区域选择性和通过的2-（1-炔基）苯甲酰胺的亲电环化循环亚胺酸酯的立体选择性合成。 a纠错
7. Synthesis of Phosphaisoquinolin-1-ones by Pd(II)-Catalyzed Cyclization of o-(1-Alkynyl)phenylphosphonamide Monoesters [O] . -1

机译：Pd（II）对磷异喹啉-1-磷酸磷素-1-催化的环化 - （1-炔基）苯基膦酰胺单酯的环化

PhI(OCOCF3)(2)-Mediated Cyclization of o-(1-Alkynyl)benzamides: Metal-Free Synthesis of 3-Hydroxy-2,3-dihydroisoquinoline-1,4-dione

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