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
相似文献
1
Rapid photoassisted access to N,O,S-polyheterocycles with benzoazocine and hydroquinoline cores: intramolecular cycloadditions of photogenerated azaxylylenes.
Angew Chem Int Ed Engl. 2011 Sep 26;50(40):9423-8. doi: 10.1002/anie.201103597. Epub 2011 Aug 31.
2
Photoassisted synthesis of enantiopure alkaloid mimics possessing unprecedented polyheterocyclic cores.
J Am Chem Soc. 2013 Jul 3;135(26):9608-11. doi: 10.1021/ja4042109. Epub 2013 Jun 21.
3
Amino Azaxylylenes Photogenerated from o-Amido Imines: Photoassisted Access to Complex Spiro-Poly-Heterocycles.
Angew Chem Int Ed Engl. 2015 Sep 21;54(39):11516-20. doi: 10.1002/anie.201504455. Epub 2015 Jun 30.
4
Oxazolines as Dual-Function Traceless Chromophores and Chiral Auxiliaries: Enantioselective Photoassisted Synthesis of Polyheterocyclic Ketones.
J Am Chem Soc. 2016 Feb 24;138(7):2110-3. doi: 10.1021/jacs.5b12690. Epub 2016 Feb 16.
5
Photoassisted diversity-oriented synthesis: accessing 2,6-epoxyazocane (oxamorphan) cores.
J Org Chem. 2014 Nov 21;79(22):10956-71. doi: 10.1021/jo5019848. Epub 2014 Nov 5.
6
Claisen rearrangement over the past nine decades.
Chem Rev. 2004 Jun;104(6):2939-3002. doi: 10.1021/cr020703u.
7
Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions.
Org Lett. 2009 Aug 20;11(16):3666-9. doi: 10.1021/ol901434g.
8
Photoassisted Synthesis of Complex Molecular Architectures: Dearomatization of Benzenoid Arenes with Aza-o-xylylenes via an Unprecedented [2+4] Reaction Topology.
Angew Chem Int Ed Engl. 2016 Jun 6;55(24):6988-91. doi: 10.1002/anie.201602288. Epub 2016 Apr 21.
9
The synthesis of an isopropyl substituted 1,4,7-triazacyclononane via an in situ sequential macrocyclisation method.
Org Biomol Chem. 2003 Jul 7;1(13):2357-63. doi: 10.1039/b302887a.
10
A facile construction of bi- or tricyclic skeletons by nickel-catalyzed stereoselective cyclization of alkynylcycloalkanone.
Org Lett. 2010 Aug 6;12(15):3494-7. doi: 10.1021/ol101329d.
引用本文的文献
1
Catalyst-free and wavelength-tuned glycosylation based on excited-state intramolecular proton transfer.
Nat Commun. 2024 Nov 7;15(1):9661. doi: 10.1038/s41467-024-54020-8.
2
Complexity-Building ESIPT-Assisted Synthesis of Fused Polyheterocyclic Sulfonamides.
Molecules. 2023 Sep 10;28(18):6549. doi: 10.3390/molecules28186549.
3
Recyclable iron(ii) caffeine-derived ionic salt catalyst in the Diels-Alder reaction of cyclopentadiene and α,β-unsaturated -acyl-oxazolidinones in dimethyl carbonate.
RSC Adv. 2019 Jul 15;9(38):21956-21963. doi: 10.1039/c9ra04098f. eCollection 2019 Jul 11.
4
Asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B.
Chem Sci. 2021 Feb 19;12(13):4747-4752. doi: 10.1039/d0sc07089k.
5
Construction of polycyclic structures with vicinal all-carbon quaternary stereocenters an enantioselective photoenolization/Diels-Alder reaction.
Chem Sci. 2021 Apr 27;12(21):7575-7582. doi: 10.1039/d1sc00883h.
6
Photoinitiated Cascade for Rapid Access to Pyrroloquinazolinone Core of Vasicinone, Luotonins, and Related Alkaloids.
Org Lett. 2019 Apr 19;21(8):2855-2858. doi: 10.1021/acs.orglett.9b00858. Epub 2019 Apr 1.
7
Photoassisted access to complex polyheterocycles containing a β-lactam moiety.
J Photochem Photobiol A Chem. 2016 Oct 1;329:182-188. doi: 10.1016/j.jphotochem.2016.07.004. Epub 2016 Jul 7.
8
Photoinduced Cycloadditions in the Diversity-Oriented Synthesis Toolbox: Increasing Complexity with Straightforward Postphotochemical Modifications.
Aust J Chem. 2015;68(11):1672-1681. doi: 10.1071/CH15266. Epub 2015 Jul 24.
9
Ti(Oi-Pr)-promoted photoenolization Diels-Alder reaction to construct polycyclic rings and its synthetic applications.
Nat Commun. 2017 Sep 20;8(1):622. doi: 10.1038/s41467-017-00440-8.
10
Photoassisted Synthesis of Complex Molecular Architectures: Dearomatization of Benzenoid Arenes with Aza-o-xylylenes via an Unprecedented [2+4] Reaction Topology.
Angew Chem Int Ed Engl. 2016 Jun 6;55(24):6988-91. doi: 10.1002/anie.201602288. Epub 2016 Apr 21.
本文引用的文献
1
A Convenient and Versatile Route to Hydroquinolines by Inter- and Intramolecular Aza-Diels-Alder Pathways.
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.
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.
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.
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.
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.
Org Biomol Chem. 2009 Apr 21;7(8):1508-24. doi: 10.1039/b817980h. Epub 2009 Feb 11.
7
Diastereoselective [4 + 4]-photocycloaddition reactions of pyran-2-ones: rapid access to functionalized 5-8-5 skeletons.
Org Lett. 2006 Aug 31;8(18):4075-8. doi: 10.1021/ol061576h.
8
Novel reaction pathways for 2-pyridone [4+4] photoadducts.
Org Lett. 2006 Jul 20;8(15):3367-70. doi: 10.1021/ol061266z.
9
Probing excited-state dynamics and intramolecular proton transfer in 1-acylaminoanthraquinones via the intermolecular solvent response.
J Phys Chem A. 2005 Aug 18;109(32):7033-45. doi: 10.1021/jp051964l.
10
Total synthesis of hamigerans and analogues thereof. Photochemical generation and Diels-Alder trapping of hydroxy-o-quinodimethanes.
J Am Chem Soc. 2004 Jan 21;126(2):613-27. doi: 10.1021/ja030498f.
Zotero 插件