芳炔与β-内酰胺和二氢喹啉酮反应中通过乙烯挤出形成吖啶酮。
Formation of acridones by ethylene extrusion in the reaction of arynes with β-lactams and dihydroquinolinones.
机构信息
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
出版信息
J Org Chem. 2012 Jul 20;77(14):6262-70. doi: 10.1021/jo3011073. Epub 2012 Jul 10.
Abstract
N-Unsubstituted β-lactams react with a molecule of aryne by insertion into the amide bond to form a 2,3-dihydroquinolin-4-one, which subsequently reacts with another molecule of aryne to form an acridone by extrusion of a molecule of ethylene. 2,3-Dihydroquinolin-4-ones react under the same reaction conditions to afford identical results. This is the first example of ethylene extrusion in aryne chemistry.
摘要
未取代的β-内酰胺与芳炔通过酰胺键插入反应形成 2,3-二氢喹啉-4-酮，后者与另一个芳炔反应通过乙烯分子的挤出形成吖啶酮。2,3-二氢喹啉-4-酮在相同的反应条件下反应，得到相同的结果。这是芳炔化学中乙烯挤出的第一个例子。
相似文献
1
Formation of acridones by ethylene extrusion in the reaction of arynes with β-lactams and dihydroquinolinones.芳炔与β-内酰胺和二氢喹啉酮反应中通过乙烯挤出形成吖啶酮。
J Org Chem. 2012 Jul 20;77(14):6262-70. doi: 10.1021/jo3011073. Epub 2012 Jul 10.
2
Ligand Controlled Regiodivergent C1 Insertion on Arynes for Construction of Phenanthridinone and Acridone Alkaloids.配体控制的芳炔 C1 插入反应构建菲啶酮和吖啶酮生物碱。
Angew Chem Int Ed Engl. 2015 Dec 1;54(49):14960-4. doi: 10.1002/anie.201508340. Epub 2015 Oct 19.
3
Synthesis of 2,3-dihydroquinolin-4(1H)-ones through catalytic metathesis of o-alkynylanilines and aldehydes.通过邻炔基苯胺与醛的催化复分解反应合成2,3-二氢喹啉-4(1H)-酮
J Org Chem. 2009 Aug 7;74(15):5644-7. doi: 10.1021/jo900857c.
4
Photoreactions with a Twist: Atropisomerism-Driven Divergent Reactivity of Enones with UV and Visible Light.具有扭转的光反应：阻转异构驱动的烯酮在紫外光和可见光下的不同反应性
Chemistry. 2016 Aug 1;22(32):11339-48. doi: 10.1002/chem.201601509. Epub 2016 Jul 6.
5
N-pyrrolylketene: a nonconjugated heteroarylketene.N-吡咯基烯酮：一种非共轭杂芳基烯酮。
Org Lett. 2011 Feb 4;13(3):494-7. doi: 10.1021/ol102837n. Epub 2010 Dec 29.
6
Chiral N-heterocyclic carbene catalyzed staudinger reaction of ketenes with imines: highly enantioselective synthesis of N-Boc beta-lactams.手性N-杂环卡宾催化的烯酮与亚胺的施陶丁格反应：N-Boc β-内酰胺的高对映选择性合成
Org Lett. 2008 Jan 17;10(2):277-80. doi: 10.1021/ol702759b. Epub 2007 Dec 18.
7
Enantioselective synthesis of aza-beta-lactams via NHC-catalyzed [2 + 2] cycloaddition of ketenes with diazenedicarboxylates.通过氮杂环卡宾催化的烯酮与二氮杂二羧酸酯的[2 + 2]环加成反应对氮杂β-内酰胺进行对映选择性合成。
J Org Chem. 2009 Oct 2;74(19):7585-7. doi: 10.1021/jo901656q.
8
BINAPHANE-catalyzed asymmetric synthesis of trans-β-lactams from disubstituted ketenes and N-tosyl arylimines.BINAPHANE 催化的二取代烯酮和 N-对甲苯磺酰基芳基亚胺的反式-β-内酰胺的不对称合成。
Org Lett. 2012 Apr 6;14(7):1784-7. doi: 10.1021/ol3003783. Epub 2012 Mar 12.
9
Diastereoselective synthesis of a bicyclic β-lactam with penicillin G-like spectrum of activity by carbonylation of an acyclic diaminocarbene.通过非环二氨基卡宾的羰基化反应，立体选择性合成具有青霉素 G 样活性的双环 β-内酰胺。
Chem Commun (Camb). 2014 Mar 4;50(18):2341-3. doi: 10.1039/c3cc48538b. Epub 2014 Jan 21.
10
Gold(I)-catalyzed regioselective cyclizations of silyl ketene amides and carbamates with alkynes.金（I）催化的甲硅烷基烯酮酰胺和氨基甲酸酯与炔烃的区域选择性环化反应。
J Org Chem. 2007 Aug 3;72(16):6287-9. doi: 10.1021/jo071014r. Epub 2007 Jul 11.
引用本文的文献
1
Skeletal Rearrangements of Amides via Breaking Inert Bonds.通过断裂惰性键实现酰胺的骨架重排
Chemistry. 2025 May;31(25):e202500595. doi: 10.1002/chem.202500595. Epub 2025 Mar 30.
2
Thioxanthone Synthesis from Thioureas through Double Aryne Insertion into a Carbon-Sulfur Double Bond.通过双芳炔插入碳-硫双键由硫脲合成噻吨酮
Org Lett. 2025 Jan 24;27(3):827-832. doi: 10.1021/acs.orglett.4c04490. Epub 2025 Jan 9.
3
Transition-Metal-Free Activation of Amide Bond by Arynes.芳炔促进酰胺键的无过渡金属活化。
Molecules. 2018 Aug 27;23(9):2145. doi: 10.3390/molecules23092145.
4
Synthesis of new tricyclic 5,6-dihydro-4-benzo[][1,2,4]triazolo[1,5-][1,4]diazepine derivatives by [3 + 2]-cycloaddition/rearrangement reactions.通过[3 + 2] - 环加成/重排反应合成新型三环5,6 - 二氢 - 4 - 苯并[][1,2,4]三唑并[1,5 - ][1,4]二氮杂卓衍生物。
Beilstein J Org Chem. 2018 Jul 18;14:1826-1833. doi: 10.3762/bjoc.14.155. eCollection 2018.
本文引用的文献
1
Regiospecific β-lactam ring-opening/recyclization reactions of N-aryl-3-spirocyclic-β-lactams catalyzed by a Lewis-Brønsted acids combined superacid catalyst system: a new entry to 3-spirocyclicquinolin-4(1H)-ones.路易斯-布朗斯台德酸复合超强酸体系催化 N-芳基-3-螺环-β-内酰胺的区域选择性β-内酰胺环开环/重排反应：3-螺环喹啉-4(1H)-酮的新入口。
Chem Commun (Camb). 2012 Jan 18;48(5):690-2. doi: 10.1039/c1cc15881c. Epub 2011 Dec 1.
2
Synthesis of 2H-indazoles by the [3 + 2] dipolar cycloaddition of sydnones with arynes.通过嗪酮与芳炔的[3 + 2]偶极环加成反应合成 2H-吲唑。
J Org Chem. 2011 Nov 4;76(21):8840-51. doi: 10.1021/jo201605v. Epub 2011 Oct 12.
3
Insertion of arynes into thioureas: a new amidine synthesis.将芳基腙插入硫脲中：一种新的脒合成方法。
Org Lett. 2011 Sep 16;13(18):4946-9. doi: 10.1021/ol202049v. Epub 2011 Aug 22.
4
Synthesis of o-(dimethylamino)aryl ketones and acridones by the reaction of 1,1-dialkylhydrazones and arynes.通过 1,1-二烷基腙和芳炔的反应合成邻-（二甲氨基）芳基酮和吖啶酮。
Org Lett. 2011 Aug 5;13(15):4136-9. doi: 10.1021/ol2016803. Epub 2011 Jul 11.
5
Aryne reaction with trifluoromethyl ketones in three modes: C-C bond cleavage, [2+2] cycloaddition and O-arylation.三氟甲基酮与 Aryne 的三种反应模式：C-C 键断裂、[2+2]环加成和 O-芳基化。
Chem Commun (Camb). 2011 Aug 14;47(30):8664-6. doi: 10.1039/c1cc12820e. Epub 2011 Jun 27.
6
The benzyne Fischer-indole reaction.苯炔费歇尔吲哚反应。
Org Lett. 2011 Jul 15;13(14):3667-9. doi: 10.1021/ol201413r. Epub 2011 Jun 14.
7
A multicomponent coupling reaction induced by insertion of arynes into the C=O bond of formamide.通过芳炔插入甲酰胺的C=O键引发的多组分偶联反应。
Angew Chem Int Ed Engl. 2011 Jul 11;50(29):6638-42. doi: 10.1002/anie.201102088. Epub 2011 May 27.
8
Three-component coupling using arynes and DMF: straightforward access to coumarins via ortho-quinone methides.通过芳炔和 DMF 的三组分偶联：通过邻醌甲醚可直接构建香豆素。
Chem Commun (Camb). 2011 Aug 14;47(30):8512-4. doi: 10.1039/c1cc11955a. Epub 2011 May 24.
9
Chroman and tetrahydroquinoline ureas as potent TRPV1 antagonists.色满和四氢喹啉脲类化合物作为强效 TRPV1 拮抗剂。
Bioorg Med Chem Lett. 2011 Mar 1;21(5):1338-41. doi: 10.1016/j.bmcl.2011.01.056. Epub 2011 Jan 21.
10
Highly selective insertion of arynes into a C(sp)-O(sp3) σ bond.高度选择性的芳炔插入 C(sp)-O(sp3) σ 键。
Org Lett. 2011 Mar 4;13(5):960-3. doi: 10.1021/ol103001k. Epub 2011 Feb 3.
Zotero 插件