2-咪唑啉酮和 2-亚氨基咪唑烷的合成。
Synthesis of 2-imidazolones and 2-iminoimidazoles.
机构信息
Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas 76019, USA.
出版信息
Org Lett. 2011 Nov 4;13(21):5736-9. doi: 10.1021/ol2022438. Epub 2011 Oct 12.
Abstract
Convenient methods for the direct conversion of imidazolium salts to the corresponding 2-imidazolone or 2-imino imidazole derivatives have been developed. Treatment of the salt with commercial bleach leads to effective oxidation at C2 and the formation of the corresponding imidazolone. Alternatively, treatment of the salt with an N-chloro amide affords the corresponding protected 2-amino derivative in good yield.
摘要
已经开发出将咪唑鎓盐直接转化为相应的 2-咪唑啉酮或 2-亚氨基咪唑衍生物的方便方法。用商业漂白剂处理盐可在 C2 处有效氧化并形成相应的咪唑啉酮。或者，用 N-氯酰胺处理盐可高产率得到相应的保护 2-氨基衍生物。
相似文献
1
Synthesis of 2-imidazolones and 2-iminoimidazoles.2-咪唑啉酮和 2-亚氨基咪唑烷的合成。
Org Lett. 2011 Nov 4;13(21):5736-9. doi: 10.1021/ol2022438. Epub 2011 Oct 12.
2
Total synthesis of 7'-desmethylkealiiquinone, 4'-desmethoxykealiiquinone, and 2-deoxykealiiquinone.7'-去甲基基奎宁酮、4'-去甲氧基基奎宁酮和 2-脱氧基奎宁酮的全合成。
J Org Chem. 2014 Mar 21;79(6):2481-90. doi: 10.1021/jo4027337. Epub 2014 Mar 3.
3
Total synthesis of 7'-desmethylkealiiquinone.7'-去甲基基拉烯醌的全合成。
Org Lett. 2012 May 4;14(9):2274-7. doi: 10.1021/ol300704w. Epub 2012 Apr 24.
4
General Installation of (4)-Imidazolone -Amide Bioisosteres Along the Peptide Backbone.在肽骨架上普遍安装（4）-咪唑啉-酰胺生物等排体。
J Am Chem Soc. 2024 May 1;146(17):11648-11656. doi: 10.1021/jacs.3c13825. Epub 2024 Apr 17.
5
N-H insertion reactions of primary ureas: the synthesis of highly substituted imidazolones and imidazoles from diazocarbonyls.伯脲的N-H插入反应：由重氮羰基化合物合成高度取代的咪唑酮和咪唑。
J Org Chem. 2004 Dec 10;69(25):8829-35. doi: 10.1021/jo048353u.
6
Design, synthesis, anticancer properties, and molecular docking of imidazolone derivatives with lipophilic moiety.含亲脂性部分的咪唑啉酮衍生物的设计、合成、抗癌特性及分子对接
Sci Rep. 2025 May 27;15(1):18537. doi: 10.1038/s41598-025-97478-2.
7
Amino acid derived 1,4-dialkyl substituted imidazolones.氨基酸衍生的 1,4-二烷基取代的咪唑啉酮。
Biopolymers. 2010;94(2):236-41. doi: 10.1002/bip.21359.
8
Rhodium carbenoid N-H insertion reactions of primary ureas: solution and solid-phase synthesis of imidazolones.伯脲的铑卡宾体N-H插入反应：咪唑酮的溶液相和固相结合合成
Org Lett. 2003 Feb 20;5(4):511-4. doi: 10.1021/ol020244j.
9
Studies toward the total synthesis of axinellamine and massadine.关于阿新那明和马萨丁全合成的研究。
Org Lett. 2007 Sep 27;9(20):3861-4. doi: 10.1021/ol0711568. Epub 2007 Sep 6.
10
Convenient synthesis of GOLD and MOLD and identification of their oxidation products in vitro and in vivo.
Amino Acids. 2007 Feb;32(2):285-9. doi: 10.1007/s00726-006-0338-6. Epub 2006 May 26.
引用本文的文献
1
Deoxyfluorination of Electron-Deficient Phenols.缺电子酚的脱氧氟化反应。
Org Lett. 2023 May 26;25(20):3649-3653. doi: 10.1021/acs.orglett.3c01018. Epub 2023 May 16.
2
Synthesis and reactivity of azole-based iodazinium salts.唑基碘嗪鎓盐的合成与反应活性
Beilstein J Org Chem. 2023 Mar 16;19:317-324. doi: 10.3762/bjoc.19.27. eCollection 2023.
3
Revealing the unusual role of bases in activation/deactivation of catalytic systems: O-NHC coupling in M/NHC catalysis.揭示碱在催化体系活化/失活中的特殊作用：M/NHC催化中的O-NHC偶联
Chem Sci. 2018 Jun 6;9(25):5564-5577. doi: 10.1039/c8sc01353e. eCollection 2018 Jul 7.
4
A facile synthetic route to benzimidazolium salts bearing bulky aromatic N-substituents.一种合成带有庞大芳香族 N-取代基的苯并咪唑鎓盐的简便路线。
Beilstein J Org Chem. 2015 Sep 17;11:1656-66. doi: 10.3762/bjoc.11.182. eCollection 2015.
5
A tandem synthesis of 5-sulfonylimino-2-imidazolones from sulfonoketenimides and dialkyl azodicarboxylates.由磺酰基烯酮亚胺和二烷基偶氮二羧酸酯串联合成5-磺酰基亚氨基-2-咪唑啉酮。
Mol Divers. 2014 Nov;18(4):721-5. doi: 10.1007/s11030-014-9529-3. Epub 2014 Jun 13.
6
Total synthesis of 7'-desmethylkealiiquinone, 4'-desmethoxykealiiquinone, and 2-deoxykealiiquinone.7'-去甲基基奎宁酮、4'-去甲氧基基奎宁酮和 2-脱氧基奎宁酮的全合成。
J Org Chem. 2014 Mar 21;79(6):2481-90. doi: 10.1021/jo4027337. Epub 2014 Mar 3.
7
Total syntheses and cytotoxicity of kealiiquinone, 2-deoxy-2-aminokealiiquinone and analogs.总合成与细胞毒性研究：基莱醌、2-脱氧-2-氨基基莱醌及类似物。
Bioorg Med Chem Lett. 2013 Nov 15;23(22):6183-7. doi: 10.1016/j.bmcl.2013.08.093. Epub 2013 Sep 6.
8
Total synthesis of 7'-desmethylkealiiquinone.7'-去甲基基拉烯醌的全合成。
Org Lett. 2012 May 4;14(9):2274-7. doi: 10.1021/ol300704w. Epub 2012 Apr 24.
本文引用的文献
1
Structure and synthesis of 2-aminoimidazole alkaloids from Leucetta and Clathrina sponges.来自 Leucetta 和 Clathrina 海绵的 2-氨基咪唑生物碱的结构与合成。
Nat Prod Rep. 2011 Mar;28(3):511-28. doi: 10.1039/c0np00001a. Epub 2010 Oct 28.
2
Asymmetric total synthesis of ent-cyclooroidin.恩环核螺甾内酯的不对称全合成。
Org Lett. 2010 Nov 5;12(21):4940-3. doi: 10.1021/ol1020916.
3
Concise total synthesis of naamine G and naamidine H.纳马宁 G 和纳马定 H 的简洁全合成。
Chem Commun (Camb). 2010 Mar 28;46(12):2148-50. doi: 10.1039/b926285g. Epub 2010 Feb 9.
4
Total Syntheses of Naamidine G and 14-Methoxynaamidine G.纳米定G和14-甲氧基纳米定G的全合成。
Tetrahedron Lett. 2010 Jan 6;51(1):164-166. doi: 10.1016/j.tetlet.2009.10.117.
5
A submarine journey: the pyrrole-imidazole alkaloids.潜艇之旅：吡咯并咪唑生物碱。
Mar Drugs. 2009 Nov 27;7(4):705-53. doi: 10.3390/md7040705.
6
Total synthesis of the putative structure of nagelamide D.纳盖拉酰胺D假定结构的全合成。
Org Lett. 2009 Apr 2;11(7):1535-8. doi: 10.1021/ol9001762.
7
Aziridination of C60 with simple amides and catalytic rearrangement of the aziridinofullerenes to azafulleroids.C60与简单酰胺的氮杂环丙烷化反应以及氮杂环丙烷富勒烯催化重排为氮杂富勒烯类化合物。
J Org Chem. 2009 Feb 20;74(4):1691-7. doi: 10.1021/jo8025737.
8
Total synthesis of (+/-)-calcaridine A and (+/-)-epi-calcaridine A.（±）-卡尔卡里定A和（±）-表卡尔卡里定A的全合成。
Org Lett. 2008 Nov 6;10(21):5055-8. doi: 10.1021/ol802018r. Epub 2008 Sep 25.
9
A new structural theme in the imidazole-containing alkaloids from a calcareous Leucetta sponge.来自钙质白枝海绵的含咪唑生物碱中的一种新结构主题。
J Org Chem. 2004 Dec 24;69(26):9025-9. doi: 10.1021/jo048789+.
10
Synthesis of the marine natural product oroidin and its Z-isomer.
J Org Chem. 2000 May 9;65(9):2806-9. doi: 10.1021/jo991395b.
Zotero 插件