Substrate-Controlled and Site-Selective[3+2]Cycloadditions of N-Heterocyclic Carbene Derived Ambident Dipoles

Ying Cheng; Mei-Fang Liu; De-Cai Fang

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Substrate-Controlled and Site-Selective[3+2]Cycloadditions of N-Heterocyclic Carbene Derived Ambident Dipoles

机译：N-杂环碳衍生的偶极子的底物控制和位点选择性[3 + 2]环加成

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2-Aryl thiocarbamoyl benzi-midazolium and imidazolinium inner salts derived from benzimidazole and imidazoline carbenes are unique ambi dent C-C-S and C-C-N 1,3-dipolar sys tems,which undergo highly efficient and site-selective cycloaddition reac tions with dimethyl acetylenedicarbox-ylate or dibenzoylacetylene to furnish spiro(imidazole-2,3'-thiophene)deriva tives in excellent yields.When treated with ethyl propiolate.methyl acrylate or acrylonitrile.spiro(imidazole-2,3-pyrrole)derivatives were formed in good yields.Theoretical studies re-vealed an asynchronous concerted mechanism for both the C-C-S and C-C-N 1,3-dipolar cycloaddition reac tions.The site selectivity in the[3+2]cycloaddition reaction of ambident 1,3-dipoles was predictably regulated by both the electronic and steric effects of dipolarophiles.

机译：衍生自苯并咪唑和咪唑啉卡宾的2-芳基硫代氨基甲酰基苯并咪唑鎓和咪唑啉鎓内盐是独特的环境CCS和CCN 1,3-偶极体系，它们通过与二甲基乙酰化乙炔基羧酸盐或二苯甲酰基乙炔进行高效且选择性的环加成反应用丙酸乙酯处理丙烯酸甲酯或丙烯腈时，形成螺（咪唑-2,3-吡咯）衍生物，收率高。理论研究揭示了CCS和CCN 1,3-偶极环加成反应的异步协同机制。环境性1,3-偶极子在[3 + 2]环加成反应中的位点选择性受电子和空间效应的调节亲极地生物。

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《Chemistry: A European journal》 |2007年第15期|共11页
作者
Ying Cheng; Mei-Fang Liu; De-Cai Fang;
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正文语种 eng
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1; 3-dipoles; carbenes; cycloaddition; heterocycles; site selectivity;

机译：1;3-偶极子;卡宾;环加成;杂环;位点选择性;

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1. Substrate-Controlled and Site-Selective[3+2]Cycloadditions of N-Heterocyclic Carbene Derived Ambident Dipoles [J] . Ying Cheng, Mei-Fang Liu, De-Cai Fang Chemistry: A European journal . 2007,第15期

机译：N-杂环碳衍生的偶极子的底物控制和位点选择性[3 + 2]环加成
2. Highly Efficient and Site-Selective [3 + 2] Cycloaddition of Carbene-Derived Ambident Dipoles with Ketenes for a Straightforward Synthesis of Spiro-Pyrrolidones [J] . Jia-Qi Li, Rong-Zhen Liao, Wan-Jian Ding, The Journal of Organic Chemistry . 2007,第16期

机译：高效，现场选择性的[3 + 2]羰基衍生的偶氮偶氮酮与酮的环加成反应，可直接合成螺吡咯烷酮。
3. HETEROANNULATION OF ALKYNYL CARBENE COMPLEXES - [3+2] DIPOLAR CYCLOADDITION OF PENTACARBONYL-[(ALKYNYL)(METHOXY)CARBENE]METALS WITH MASKED 1,3-DIPOLES [J] . Choi YH., Yoon YJ., Kim JN., Synthetic Communications . 1995,第14期

机译：炔基碳复合物的异壬二烯化-[3 + 2]戊烯基-[（炔基）（甲氧基）碳素]金属与掩蔽的1,3-二甲醚的[3 + 2]二元循环负载
4. Synthesis of 2-trifluoromethyl-substituted five-membered N-heterocyclic compoundsvia decarboxylative 3+2 cycloaddition [C] . Qian Liu, Kengo Akagawa, Kazuaki Kudo 日本化学会春季年会 . 2020

机译：合成2-三氟甲基取代的五元氮杂环化合物脱羧3 + 2环加成
5. Novel aza-Prins cyclization and [3+2] dipolar cycloaddition toward N-heterocyclic molecules and studies toward the total synthesis of borrecapine. [D] . Liu, Xiaoxi. 2014

机译：新型氮杂-Prins环化和向N杂环分子的[3 + 2]偶极环加成反应，并向硼烷总合成进行研究。
6. Ru(II)-Catalyzed Mild 3+2 Carbocyclization with Aromatic N-H Ketimines and Internal Alkynes Using N-Heterocyclic Carbene (NHC) Ligands [O] . Ms. Jing Zhang, Dr. Angel Ugrinov, Prof. Dr. Pinjing Zhao -1

机译：Ru（II）催化使用N-杂环卡宾（NHC）配体与芳族N-H酮亚胺和内部炔烃进行的轻度3 + 2碳环化。
7. Enantioselective N-heterocyclic carbene catalyzed formal 3+2 cycloaddition using α-aroyloxyaldehydes and oxaziridines [O] . Kerr Ryan W. F., Greenhalgh Mark D., Slawin Alexandra M. Z., 2017

机译：对映选择性N-杂环卡宾使用α-芳酰氧基醛和恶唑烷催化的正式3 + 2环加成反应

Substrate-Controlled and Site-Selective[3+2]Cycloadditions of N-Heterocyclic Carbene Derived Ambident Dipoles

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