One-pot cascade synthesis of 2,3-disubstituted 2,3-dihydrobenzofurans via ortho-quinone methide intermediates generated in situ

Shaikh Abdul Kadar; Varvounis George

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One-pot cascade synthesis of 2,3-disubstituted 2,3-dihydrobenzofurans via ortho-quinone methide intermediates generated in situ

机译：通过原位产生的邻醌甲基中间体的2,3-二磺酸2,3-二氢苯并呋喃的一锅级联合成

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A simple and efficient one-pot cascade reaction for the regioselective synthesis of trans or cis/trans 2,3-disubstituted 2,3-dihydrobenzofurans is reported. The method involves fluoride-induced desilylation, generation of o-quinone methide (o-QM) by chloride or nitrate anion elimination, Michael addition and intramolecular 5-exo-tet elimination of a bromide anion. Nitrate, acetoxy and chloride anions are compared as leaving groups in the formation of the in situ generated o-QM.

机译：报道了一种简单且有效的一罐用于反式或顺式/反式2,3-二取代的2,3-二氢苯并呋喃的分区域合成的单盆级联反应。该方法涉及氟化物诱导的脱脂，通过氯化物或硝酸盐阴离子消除产生O-醌甲基（O-QM），迈克尔加成和分子内5- X型TET消除溴化物阴离子。将硝酸盐，乙酰氧基和氯化物阴离子进行比较，因为在原位产生的O-QM形成中，将基团进行比较。

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《RSC Advances》 |2015年第19期|共5页
作者
Shaikh Abdul Kadar; Varvounis George;
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Univ Ioannina Dept Chem Sect Organ Chem &

Biochem GR-45110 Ioannina Greece;

Univ Ioannina Dept Chem Sect Organ Chem &

Biochem GR-45110 Ioannina Greece;

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正文语种 eng
中图分类化学;
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1. One-pot cascade synthesis of 2,3-disubstituted 2,3-dihydrobenzofurans via ortho-quinone methide intermediates generated in situ [J] . Shaikh Abdul Kadar, Varvounis George RSC Advances . 2015,第19期

机译：通过原位产生的邻醌甲基中间体的2,3-二磺酸2,3-二氢苯并呋喃的一锅级联合成
2. Direct Propargylation of ortho-Quinone Methides with Alkynyl Zinc Reagents: An Application to the One-Pot Synthesis of 2,3-Disubstituted Benzofurans [J] . Sun Manman, Song Jinyu, Wang Lei, Synlett . 2020,第8期

机译：用炔基试剂直接对邻醌甲基甲基磷酸酯的丙基：施用2,3-二取代的苯并呋喃的单罐合成
3. Asymmetric Synthesis of 2,3-Dihydrobenzofurans by a [4+1] Annulation Between Ammonium Ylides and In Situ Generated o-Quinone Methides [J] . Nicole Meisinger, Lukas Roiser, Uwe Monkowius, Chemistry: A European journal . 2017,第21期

机译：2,3-二氢苯并呋喃的不对称合成[4 + 1]环核和原位产生的O-醌甲基化物
4. SYNTHESIS OF 2,3-DIHYDROBENZOFURAN DERIVATIVES VIA ELECTRON TRANSFER REACTION CATALYZED BY IRON(III)-SALT IN AN IONIC LIQUID SOLVENT SYSTEM [C] . Toshiyuki Itoh, Hiroyuki Uehara, Kimio Kawai, Proceedings vol.2004-10; International Manuel M. Baizer Symposium in Honor of Dennis H. Evans and Masao Tokuda and Meeting of the Electrochemical Society; 20040509-14; San Antonio,TX(US) . 2004

机译：离子液体溶剂中铁（III）-盐催化的电子转移反应合成2,3-二羟基苯并呋喃衍生物
5. Simultaneous synthesis of both rings of chromenes via a benzannulation/ortho-quinone methide formation/electrocyclization cascade and an approach towards the asymmetric synthesis of chromenes [D] . Majumdar, Nilanjana 2012

机译：通过苯环化/邻醌甲基化物形成/电环化级联同时合成二甲基苯酮的环和不对称合成二苯甲基苯的方法
6. Asymmetric Synthesis of 23‐Dihydrobenzofurans by a 4+1 Annulation Between Ammonium Ylides and In Situ Generated o‐Quinone Methides [O] . Nicole Meisinger, Lukas Roiser, Prof. Uwe Monkowius, -1

机译：铵盐和原位生成的邻苯二甲腈间的4 + 1环状不对称合成23-二氢苯并呋喃
7. Stereodivergent Synthesis of Enantioenriched 2,3-Disubstituted Dihydrobenzofurans via a One-Pot CH Functionalization/Oxa-Michael Addition Cascade [O] . -1

机译：通过单壶CH官能化/ OXA-MICHAEL加成级联通过单氨基化2,3-二取代二氢苯甲苄酯的Stereodieled合成

One-pot cascade synthesis of 2,3-disubstituted 2,3-dihydrobenzofurans via ortho-quinone methide intermediates generated in situ

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