Rapid photoassisted access to N,O,S-polyheterocycles with benzoazocine and hydroquinoline cores: intramolecular cycloadditions of photogenerated azaxylylenes.
作者信息
Mukhina Olga A, Kumar N N Bhuvan, Arisco Teresa M, Valiulin Roman A, Metzel Greg A, Kutateladze Andrei G
机构信息
Department of Chemistry and Biochemistry, University of Denver, Denver, CO 80208-2436, USA.
出版信息
Angew Chem Int Ed Engl. 2011 Sep 26;50(40):9423-8. doi: 10.1002/anie.201103597. Epub 2011 Aug 31.
Abstract
摘要
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1
A Convenient and Versatile Route to Hydroquinolines by Inter- and Intramolecular Aza-Diels-Alder Pathways.通过分子间和分子内氮杂-狄尔斯-阿尔德途径合成对苯二酚喹啉的便捷通用方法。
Angew Chem Int Ed Engl. 1999 Jul 12;38(13-14):1928-1931. doi: 10.1002/(SICI)1521-3773(19990712)38:13/14<1928::AID-ANIE1928>3.0.CO;2-1.
2
ESIPT-mediated photocycloadditions of 3-hydroxyquinolinones: development of a fluorescence quenching assay for reaction screening.ESIPT 介导的 3-羟基喹啉酮的光环加成反应：反应筛选的荧光猝灭测定法的建立。
Org Lett. 2011 Mar 18;13(6):1346-9. doi: 10.1021/ol200032f. Epub 2011 Feb 21.
3
Tetraquinanes via [4 + 4] photocycloaddition/transannular ring closure.四环烷通过[4 + 4]光环加成/跨环环闭合反应生成。
Org Lett. 2010 Oct 15;12(20):4510-2. doi: 10.1021/ol101802s.
4
Positive identification of UV-generated, non-hydrogen-bonded isomers of o-hydroxybenzaldehyde and o-hydroxyacetophenone.鉴定紫外线照射下生成的邻羟基苯甲醛和邻羟基苯乙酮的非氢键异构体。
J Phys Chem A. 2010 May 6;114(17):5588-95. doi: 10.1021/jp1003775.
5
New strategies for the design of folded peptoids revealed by a survey of noncovalent interactions in model systems.新型折叠肽设计策略的揭示：模型体系中非共价相互作用研究
J Am Chem Soc. 2009 Nov 18;131(45):16555-67. doi: 10.1021/ja907184g.
6
Structure-function relationships in peptoids: recent advances toward deciphering the structural requirements for biological function.类肽中的结构-功能关系：解析生物学功能结构要求的最新进展
Org Biomol Chem. 2009 Apr 21;7(8):1508-24. doi: 10.1039/b817980h. Epub 2009 Feb 11.
7
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Org Lett. 2006 Aug 31;8(18):4075-8. doi: 10.1021/ol061576h.
8
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Org Lett. 2006 Jul 20;8(15):3367-70. doi: 10.1021/ol061266z.
9
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J Phys Chem A. 2005 Aug 18;109(32):7033-45. doi: 10.1021/jp051964l.
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J Am Chem Soc. 2004 Jan 21;126(2):613-27. doi: 10.1021/ja030498f.
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