新型苯并-1,3-二恶烷并、苯并噻唑并、吡啶并和喹啉并-5H-苯并[d]-吡唑并[5,1-b][1,3]-恶嗪和 1H-吡唑的简便合成方法。
Facile syntheses of novel benzo-1,3-dioxolo-, benzothiazolo-, pyrido-, and quinolino-fused 5H-benzo[d]-pyrazolo[5,1-b][1,3]-oxazines and 1H-pyrazoles.
机构信息
Department of Chemistry, University of California, Davis, California 95616, USA.
出版信息
Org Lett. 2011 Mar 4;13(5):1060-3. doi: 10.1021/ol103108z. Epub 2011 Feb 4.
Abstract
A number of novel benzo-1,3-dioxolo-, benzothiazolo-, pyrido-, and quinolino-fused 5H-benzo[d]pyrazolo[5,1-b][1,3]-oxazines and 1H-pyrazoles were synthesized utilizing an easy and effective N,N-bond forming heterocyclization reaction. In so doing, the substrate scope of this heterocyclization reaction, which starts with o-nitroheterocyclic aldehydes, was expanded to provide several unique heterocyclic compounds for biological screening. This work further demonstrates the versatility of this simple, base-mediated, one-pot heterocyclization method in the construction of novel heterocycles.
摘要
利用一种简单有效的 N，N 键形成杂环化反应，合成了一系列新型苯并-1,3-二恶烷、苯并噻唑、吡啶并、喹啉并 5H-苯并[d]吡唑并[5,1-b][1,3]-恶嗪和 1H-吡唑。在这种情况下，该杂环化反应的底物范围扩大，以包含邻硝基杂环醛，为生物筛选提供了几种独特的杂环化合物。这项工作进一步证明了这种简单、基于碱的一锅法杂环化方法在构建新型杂环中的多功能性。
相似文献
1
Facile syntheses of novel benzo-1,3-dioxolo-, benzothiazolo-, pyrido-, and quinolino-fused 5H-benzo[d]-pyrazolo[5,1-b][1,3]-oxazines and 1H-pyrazoles.新型苯并-1,3-二恶烷并、苯并噻唑并、吡啶并和喹啉并-5H-苯并[d]-吡唑并[5,1-b][1,3]-恶嗪和 1H-吡唑的简便合成方法。
Org Lett. 2011 Mar 4;13(5):1060-3. doi: 10.1021/ol103108z. Epub 2011 Feb 4.
2
A facile synthesis of new 5H-indazolo[3,2-b]benzo[d]-1,3-oxazines via one-pot intramolecular Bis-heterocyclizations.通过一锅法分子内双杂环化反应简便合成新型5H-吲唑并[3,2-b]苯并[d]-1,3-恶嗪。
J Org Chem. 2008 Jan 4;73(1):234-40. doi: 10.1021/jo702067z. Epub 2007 Dec 4.
3
One-step construction of tetrahydro-5H-indolo[3,2-c]quinolines from benzyl azides and indoles via a cascade reaction sequence.一步法通过苄基叠氮化物和吲哚的级联反应序列构建四氢-5H-吲哚并[3,2-c]喹啉。
Org Lett. 2011 Dec 16;13(24):6331-3. doi: 10.1021/ol202656u. Epub 2011 Nov 10.
4
Catalytic and highly regioselective cross-coupling of aromatic C-H substrates.芳香族C-H底物的催化及高区域选择性交叉偶联反应。
J Am Chem Soc. 2007 Oct 3;129(39):11904-5. doi: 10.1021/ja074395z. Epub 2007 Sep 11.
5
Three-component Povarov reaction-heteroannulation with arynes: synthesis of 5,6-dihydroindolo[1,2-a]quinolines.三组分 Povarov 反应-杂芳构化：5,6-二氢吲哚并[1,2-a]喹啉的合成。
Org Lett. 2014 Mar 21;16(6):1756-9. doi: 10.1021/ol500447r. Epub 2014 Feb 28.
6
Synthesis of the core ring system of the yuzurimine-type Daphniphyllum alkaloids by cascade condensation, cyclization, cycloaddition chemistry.通过级联缩合、环化、环加成化学合成鱼藤素型千金藤生物碱的核心环系统。
J Org Chem. 2011 Apr 1;76(7):2360-6. doi: 10.1021/jo2000868. Epub 2011 Mar 8.
7
Metal-Free Decarboxylative Cyclization/Ring Expansion: Construction of Five-, Six-, and Seven-Membered Heterocycles from 2-Alkynyl Benzaldehydes and Cyclic Amino Acids.无金属脱羧环化/环扩张：2-炔基苯甲醛和环状氨基酸构建五、六、七元杂环。
Angew Chem Int Ed Engl. 2015 Aug 10;54(33):9564-7. doi: 10.1002/anie.201504429. Epub 2015 Jul 6.
8
Synthesis of 2-substituted pyrazolo[1,5-a]pyridines through cascade direct alkenylation/cyclization reactions.通过级联直接烯丙基化/环化反应合成 2-取代的吡唑并[1,5-a]吡啶。
Org Lett. 2010 Feb 5;12(3):516-9. doi: 10.1021/ol902710f.
9
A versatile synthesis of pyrazolo[3,4-c]isoquinoline derivatives by reaction of 4-aryl-5-aminopyrazoles with aryl/heteroaryl aldehydes: the effect of the heterocycle on the reaction pathways.通过4-芳基-5-氨基吡唑与芳基/杂芳基醛反应实现吡唑并[3,4-c]异喹啉衍生物的通用合成：杂环对反应途径的影响
Org Biomol Chem. 2005 Mar 7;3(5):932-40. doi: 10.1039/b417002d. Epub 2005 Feb 8.
10
A one-pot regioselective synthesis of benzo[d]imidazo[2,1-b]thiazoles.一锅法区域选择性合成苯并[d]咪唑并[2,1-b]噻唑。
Org Biomol Chem. 2012 Oct 21;10(39):7944-8. doi: 10.1039/c2ob26211h.
引用本文的文献
1
Davis-Beirut Reaction: Diverse Chemistries of Highly Reactive Nitroso Intermediates in Heterocycle Synthesis.戴维斯-贝鲁特反应：杂环合成中高反应性亚硝酰中间体的多样化学反应性。
Acc Chem Res. 2019 Aug 20;52(8):2256-2265. doi: 10.1021/acs.accounts.9b00220. Epub 2019 Jul 22.
2
Inhibition of myeloperoxidase: evaluation of 2H-indazoles and 1H-indazolones.髓过氧化物酶的抑制作用：2H-吲唑和1H-吲唑酮的评估
Bioorg Med Chem. 2014 Nov 15;22(22):6422-9. doi: 10.1016/j.bmc.2014.09.044. Epub 2014 Oct 2.
3
Davis-Beirut reaction: route to thiazolo-, thiazino-, and thiazepino-2H-indazoles.戴维斯-贝鲁特反应：通往噻唑并、噻嗪并和噻氮杂卓并-2H-吲唑的途径。
J Org Chem. 2014 Aug 1;79(15):6939-45. doi: 10.1021/jo501014e. Epub 2014 Jul 23.
4
Acid and base catalyzed Davis-Beirut reaction: experimental and theoretical mechanistic studies and synthesis of novel 3-amino-2H-indazoles.酸和碱催化的戴维斯-贝鲁特反应：实验与理论机理研究及新型3-氨基-2H-吲唑的合成
Tetrahedron Lett. 2012 Nov 28;53(48):6475-6478. doi: 10.1016/j.tetlet.2012.09.026. Epub 2012 Sep 15.
5
A one-pot-three-step route to triazolotriazepinoindazolones from oxazolino-2H-indazoles.唑啉并-2H-吲唑一锅三步法制备三唑并三氮唑并吲哚酮。
Org Lett. 2012 Aug 3;14(15):3870-3. doi: 10.1021/ol3015804. Epub 2012 Jul 23.
6
The Davis-Beirut reaction: N1,N2-disubstituted-1H-indazolones via 1,6-electrophilic addition to 3-alkoxy-2H-indazoles.戴维斯-贝鲁特反应：通过 3-烷氧基-2H-吲唑的 1,6-亲电加成反应得到 N1,N2-二取代-1H-吲唑酮。
Org Lett. 2011 Jun 17;13(12):3138-41. doi: 10.1021/ol2010424. Epub 2011 May 25.
本文引用的文献
1
4-(Pyrazol-4-yl)-pyrimidines as selective inhibitors of cyclin-dependent kinase 4/6.4-(吡唑-4-基)嘧啶类作为细胞周期蛋白依赖性激酶 4/6 的选择性抑制剂。
J Med Chem. 2010 Nov 25;53(22):7938-57. doi: 10.1021/jm100571n. Epub 2010 Nov 1.
2
Synthesis of 2H-indazoles by the [3 + 2] cycloaddition of arynes and sydnones.通过芳炔与 sydnones 的 [3 + 2] 环加成反应合成 2H-吲唑。
Org Lett. 2010 May 21;12(10):2234-7. doi: 10.1021/ol100586r.
3
An oxazolo[3,2-b]indazole route to 1H-indazolones.一种通过恶唑并[3,2 - b]吲唑合成1H - 吲唑酮的路线。
Org Lett. 2009 Jul 2;11(13):2760-3. doi: 10.1021/ol900891s.
4
A facile synthesis of new 5H-indazolo[3,2-b]benzo[d]-1,3-oxazines via one-pot intramolecular Bis-heterocyclizations.通过一锅法分子内双杂环化反应简便合成新型5H-吲唑并[3,2-b]苯并[d]-1,3-恶嗪。
J Org Chem. 2008 Jan 4;73(1):234-40. doi: 10.1021/jo702067z. Epub 2007 Dec 4.
5
Rapid access to pyrazolo[3,4-c]pyridines via alkyne annulation: limitations of steric control in nickel-catalyzed alkyne insertions.通过炔烃环化快速合成吡唑并[3,4-c]吡啶：镍催化炔烃插入反应中空间控制的局限性
Org Lett. 2007 Nov 22;9(24):4947-50. doi: 10.1021/ol701784w. Epub 2007 Nov 3.
6
Syntheses of potent, selective, and orally bioavailable indazole-pyridine series of protein kinase B/Akt inhibitors with reduced hypotension.具有降低低血压作用的强效、选择性且口服生物可利用的吲唑-吡啶系列蛋白激酶B/Akt抑制剂的合成。
J Med Chem. 2007 Jun 28;50(13):2990-3003. doi: 10.1021/jm0701019. Epub 2007 May 25.
7
Synthesis of a library of 2-alkyl-3-alkyloxy-2H-indazole-6-carboxamides.2-烷基-3-烷氧基-2H-吲唑-6-甲酰胺文库的合成
J Comb Chem. 2007 Jan-Feb;9(1):171-7. doi: 10.1021/cc060109o.
8
N,N-bond-forming heterocyclization: synthesis of 3-alkoxy-2H-indazoles.N，N-键形成的杂环化反应：3-烷氧基-2H-吲唑的合成
J Org Chem. 2006 Mar 31;71(7):2687-9. doi: 10.1021/jo0524831.
9
Synthesis of N2-(substituted benzyl)-3-(4-methylphenyl)indazoles as novel anti-angiogenic agents.新型抗血管生成剂N2-（取代苄基）-3-（4-甲基苯基）吲唑的合成
Bioorg Med Chem. 2006 Jan 15;14(2):528-36. doi: 10.1016/j.bmc.2005.08.032. Epub 2005 Oct 3.
10
Claimed 2,1-benzisoxazoles are indazalones.所要求保护的2,1-苯并异恶唑类为吲唑酮类。
J Org Chem. 2005 Feb 4;70(3):1060-2. doi: 10.1021/jo048153i.
Zotero 插件