分子碘介导的含杂原子的烯基或炔基体系的连接环化反应。
Molecular iodine-mediated cyclization of tethered heteroatom-containing alkenyl or alkynyl systems.
机构信息
Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South Africa.
出版信息
Molecules. 2009 Nov 25;14(12):4814-37. doi: 10.3390/molecules14124814.
Abstract
Molecular iodine has established itself as a readily available and easy-to-handle electrophilic and oxidizing reagent used in various organic transformations. In this review attention is focused on the use of molecular iodine in promoting cyclization (iodocyclization and cyclodehydroiodination) of tethered heteroatom-containing alkenyl or alkynyl systems.
摘要
分子碘已被确立为一种易得且易于处理的亲电试剂和氧化剂，用于各种有机转化。在这篇综述中，重点关注了分子碘在促进含杂原子的烯基或炔基连接体系的环化（碘环化和环脱氢碘化）反应中的应用。
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2
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Eur J Med Chem. 2009 Mar;44(3):1278-87. doi: 10.1016/j.ejmech.2008.08.008. Epub 2008 Sep 3.
3
Iodocarbocyclization reaction of beta-ketoesters and alkynes.
Org Lett. 2007 Jul 19;9(15):2823-6. doi: 10.1021/ol0710459. Epub 2007 Jun 22.
4
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Bioorg Med Chem Lett. 2007 Jun 1;17(11):3212-6. doi: 10.1016/j.bmcl.2007.03.016. Epub 2007 Mar 12.
5
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Selective endo and exo iodocyclizations in the synthesis of quinolines and indoles.
Org Lett. 2006 Jan 19;8(2):243-6. doi: 10.1021/ol052518j.
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Iodo- and bromo-enolcyclization of 2-(2-propenyl)cyclohexanediones and 2-(2-propenyl)cyclohexenone derivatives using iodine in methanol and pyridinium hydrobromide perbromide in dichloromethane.
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