3-氨基喹啉置于potassium Nitrite,氢溴酸,二甲基亚砜体系中,用 水 作为反应溶剂,化学反应 0.5H,以59%的收率获得产物3-溴喹啉 参考文献:Efficient One-Pot Transformation Of Aminoarenes To Haloarenes Using Halodimethylisulfonium Halides Generated In Situ 标题:Efficient One-Pot Transformation Of Aminoarenes To Haloarenes Using Halodimethylisulfonium Halides Generated In Situ 摘要:卤二甲基亚砜卤化物1是一种非常好的亲核卤化物,可在现场由氢卤酸和二甲亚砜形成.这种活化的亲核卤化物迅速将由相同的氢卤酸和亚硝酸根在现场制备的芳基重氮盐转化为芳基氯化物,溴化物或碘化物,收率较高.在dmso中,亚硝酸根和氢卤酸的联合作用是直接转化芳香胺的必要条件,从而在1小时内产生芳基卤化物.带有电子给体或吸引基团或有立体位阻的芳香胺的取代化合物也可顺利转化为相应的芳香卤化物.观测到的唯一副产物是去氨基芳烃(通常<7%).孤立的芳基重氮盐也可以使用1转化为相应的芳基卤化物.该方法提供了一种简便的,一步法的程序,用于将氨基芳烃转化为卤代芳烃,并且不伴随通常伴随使用铜卤化物进行桑迈尔反应的环境污染物.关键词:氨基芳烃,卤代芳烃,卤二甲基亚砜卤化物,卤化,胺化. DOI:10.1139/v05-026
专利号:US-9982005-B2 优先权日:2013-04-04 标 题 :Macrolides and methods of their preparation and use 发明人:MYERS ANDREW G; SEIPLE IAN BASS; ZHANG ZIYANG 权利人:HARVARD COLLEGE 摘要:Provided herein are methods of preparing macrolides by the coupling of an eastern and western half, followed by macrocyclization, to provide macrolides, including both known and novel macrolides. Intermediates in the synthesis of macrolides including the eastern and western halves are also provided. Pharmaceutical compositions and methods of treating infectious diseases and inflammatory conditions using the inventive macrolides are also provided. A general diastereoselective aldol methodology used in the synthesis of the western half is further provided.
专利号:US-6316675-B1 优先权日:1997-03-25 标 题:Process for the preparation of an olefin-substituted aromatic or heteroaromatic compound 发明人:REETZ MANFRED T; LOHMER GUNTHER; LOHMER RENATE 权利人:STUDIENGESELLSCHAFT KOHLE MBH 摘要:A process for the synthesis of olefins having aromatic substituents is described in which olefins are reacted with aryl halides in the presence of catalysts consisting of palladium compounds and tetraaryl phosphonium salts.
专利号:WO-2015131100-A1 优先权日:2014-02-28 标题:Ligand-controlled c(sp3)-h arylation and olefination in synthesis of unnatural chiral alpha amino acids 发明人:YU JIN-QUAN 权利人:SCRIPPS RESEARCH INST 摘要:The use of ligands to tune the reactivity and selectivity of transition metal-catalysts for C(-sp3)-H bond functionalization is a central challenge in synthetic organic chemistry. Herein, we report a rare example of catalyst-controlled C(sp3)-H arylation using pyridine and quinoline derivatives: the former promotes exclusive monoarylation, whereas the latter activates the catalyst further to achieve diarylation. Successive application of these ligands enables the sequential diarylation of a methyl group in an alanine derivative with two different aryl iodides, affording a wide range of β-Ar-p-Ar ' -cc-amino acids with excellent levels of diastereoselectivity (d.r. > 20:1). Both configurations of the β-chiral center can be accessed by choosing the order in which the aryl groups are installed. The use of a quinoline derivative as a ligand also enables C(sp3)-H olefination of a protected alanine.
专利号:WO-2008054857-A1 优先权日:2006-11-01 标 题:Process for the preparation of intermediates useful in the treatment of hiv infection 发明人:MARTIN MICHAEL TOLAR 权利人:SMITHKLINE BEECHAM CORP; MARTIN MICHAEL TOLAR 摘要:The present invention is directed to processes for the synthesis of intermediates useful in the preparation of non-nucleoside reverse transcriptase inhibitors.
专利号:US-7071314-B2 优先权日:2001-05-30 标题:Arylation method for the functionalization of O-allyl erythromycin derivatives 发明人:ZHANG WEIJANG; HSU MARGARET CHI-PING; HAIGHT ANTHONY R; PETERSON MATTHEW JOHN; NARAYANAN BIKSHANDARKOIL A 权利人:ABBOTT LAB 摘要:An efficient arylation technique for use in the synthesis of erythromycin derivatives, involving a modified Heck reaction which employs less than six mole percent of palladium catalyst and no phosphine is disclosed. With this modified Heck reaction, an O-alkenylaryl macrolide can be obtained in a much shorter reaction time than under conventional Heck reaction conditions. The modified Heck reaction can be utilized in a method for phosphine-free arylation of an O-allylic erythromycin derivative, in a method for preparing an O-alkenylaryl erythromycin A derivative, or in a method for preparing a 2′, 4″-hydroxyl protected 6-O-alkenylaryl erythromycin A derivative.
专利号:US-7074932-B2 优先权日:1999-06-24 标题 :Preparation of quinoline-substituted carbonate and carbamate derivatives 发明人:ALLEN MICHAEL S; PREMCHANDRAN RAMIYA H; CHANG SOU-JEN; CONDON STEPHEN; DEMATTEI JOHN A; KING STEVEN A; KOLACZKOWSKI LAWRENCE; MANNA SUKUMAR; NICHOLS PAUL J; PATEL HEMANT H; PATEL SUBHASH R; PLATA DANIEL J; STONER ERIC J; TIEN JIEN-HEH J; WITTENBERGER STEVEN J 权利人:ALLEN MICHAEL S; PREMCHANDRAN RAMIYA H; CHANG SOU-JEN; CONDON STEPHEN; DEMATTEI JOHN A; KING STEVEN A; KOLACZKOWSKI LAWRENCE; MANNA SUKUMAR; NICHOLS PAUL J; PATEL HEMANT H; PATEL SUBHASH R; PLATA DANIEL J; STONER ERIC J; TIEN JIEN-HEH J; WITTENBERGER STEVEN J 摘要:The invention relates to a process for preparing quinoline-substituted carbonate and carbamate compounds, which are important intermediates in the synthesis of 6-O-substituted macrolide antibiotics. The process employs metal-catalyzed coupling reactions to provide a carbonate or carbamate of formula (I) or (II) or a substrate that can be reduced to obtain the same.
[参考文献]: Bin Yang, Et Al. Prediction Of Setschenow Constants Of N-Heteroaromatics In Nacl Solutions Based On The Partial Charge On The Heterocyclic Nitrogen Atom. Environ Sci Pollut Res Int. 2016 Feb;23(4):3399-405.
合成参考文献
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