tert-Butyl Nitrite-Induced Radical Nitrile Oxidation Cycloaddition: Synthesis of Isoxazole/Isoxazoline-Fused Benzo 6/7/8-membered Oxacyclic Ketones
A practical metal-free and additive-free approach for the synthesis of 6/7/8-membered oxacyclic ketone-fused isoxazoles/isoxazolines tetracyclic or tricyclic structures is reported through Csp3–H bond radical nitrile oxidation and the intramolecular cycloaddition of alkenyl/alkynyl-substituted aryl...
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| Published in | Molecules (Basel, Switzerland) Vol. 29; no. 6; p. 1202 |
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| Main Authors | , , , , , , , , , |
| Format | Journal Article |
| Language | English |
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MDPI AG
07.03.2024
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| ISSN | 1420-3049 1420-3049 |
| DOI | 10.3390/molecules29061202 |
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| Abstract | A practical metal-free and additive-free approach for the synthesis of 6/7/8-membered oxacyclic ketone-fused isoxazoles/isoxazolines tetracyclic or tricyclic structures is reported through Csp3–H bond radical nitrile oxidation and the intramolecular cycloaddition of alkenyl/alkynyl-substituted aryl methyl ketones. This convenient approach enables the simultaneous formation of isoxazole/isoxazoline and 6/7/8-membered oxacyclic ketones to form polycyclic architectures by using tert-butyl nitrite (TBN) as a non-metallic radical initiator and N–O fragment donor. |
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| AbstractList | A practical metal-free and additive-free approach for the synthesis of 6/7/8-membered oxacyclic ketone-fused isoxazoles/isoxazolines tetracyclic or tricyclic structures is reported through Csp3–H bond radical nitrile oxidation and the intramolecular cycloaddition of alkenyl/alkynyl-substituted aryl methyl ketones. This convenient approach enables the simultaneous formation of isoxazole/isoxazoline and 6/7/8-membered oxacyclic ketones to form polycyclic architectures by using tert-butyl nitrite (TBN) as a non-metallic radical initiator and N–O fragment donor. A practical metal-free and additive-free approach for the synthesis of 6/7/8-membered oxacyclic ketone-fused isoxazoles/isoxazolines tetracyclic or tricyclic structures is reported through C sp 3 –H bond radical nitrile oxidation and the intramolecular cycloaddition of alkenyl/alkynyl-substituted aryl methyl ketones. This convenient approach enables the simultaneous formation of isoxazole/isoxazoline and 6/7/8-membered oxacyclic ketones to form polycyclic architectures by using tert -butyl nitrite (TBN) as a non-metallic radical initiator and N–O fragment donor. A practical metal-free and additive-free approach for the synthesis of 6/7/8-membered oxacyclic ketone-fused isoxazoles/isoxazolines tetracyclic or tricyclic structures is reported through C -H bond radical nitrile oxidation and the intramolecular cycloaddition of alkenyl/alkynyl-substituted aryl methyl ketones. This convenient approach enables the simultaneous formation of isoxazole/isoxazoline and 6/7/8-membered oxacyclic ketones to form polycyclic architectures by using -butyl nitrite (TBN) as a non-metallic radical initiator and N-O fragment donor. A practical metal-free and additive-free approach for the synthesis of 6/7/8-membered oxacyclic ketone-fused isoxazoles/isoxazolines tetracyclic or tricyclic structures is reported through Csp3-H bond radical nitrile oxidation and the intramolecular cycloaddition of alkenyl/alkynyl-substituted aryl methyl ketones. This convenient approach enables the simultaneous formation of isoxazole/isoxazoline and 6/7/8-membered oxacyclic ketones to form polycyclic architectures by using tert-butyl nitrite (TBN) as a non-metallic radical initiator and N-O fragment donor.A practical metal-free and additive-free approach for the synthesis of 6/7/8-membered oxacyclic ketone-fused isoxazoles/isoxazolines tetracyclic or tricyclic structures is reported through Csp3-H bond radical nitrile oxidation and the intramolecular cycloaddition of alkenyl/alkynyl-substituted aryl methyl ketones. This convenient approach enables the simultaneous formation of isoxazole/isoxazoline and 6/7/8-membered oxacyclic ketones to form polycyclic architectures by using tert-butyl nitrite (TBN) as a non-metallic radical initiator and N-O fragment donor. |
| Author | Yang, Chuan-Ming Cao, Tian-Zheng Li, Ya-Chen Dong, Qiao-Ke Yue, Qian-Wen Ma, Ying Zhang, Hong-Xi Sun, Yuan-Yuan Cao, Jian-Kang Zhu, Yan-Ping |
| AuthorAffiliation | 2 Anhui Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, China 1 Key Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, School of Pharmacy, Yantai University, Yantai 264005, China; cjk18954343136@163.com (J.-K.C.); tianzheng202201@163.com (T.-Z.C.); 19553508187@163.com (Q.-W.Y.); 15935574380@163.com (Y.M.); 15254990262@163.com (C.-M.Y.); 13355081055@163.com (H.-X.Z.); a2732586174@163.com (Y.-C.L.); 19558912885@163.com (Q.-K.D.) |
| AuthorAffiliation_xml | – name: 2 Anhui Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, China – name: 1 Key Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, School of Pharmacy, Yantai University, Yantai 264005, China; cjk18954343136@163.com (J.-K.C.); tianzheng202201@163.com (T.-Z.C.); 19553508187@163.com (Q.-W.Y.); 15935574380@163.com (Y.M.); 15254990262@163.com (C.-M.Y.); 13355081055@163.com (H.-X.Z.); a2732586174@163.com (Y.-C.L.); 19558912885@163.com (Q.-K.D.) |
| Author_xml | – sequence: 1 givenname: Jian-Kang surname: Cao fullname: Cao, Jian-Kang – sequence: 2 givenname: Tian-Zheng surname: Cao fullname: Cao, Tian-Zheng – sequence: 3 givenname: Qian-Wen surname: Yue fullname: Yue, Qian-Wen – sequence: 4 givenname: Ying surname: Ma fullname: Ma, Ying – sequence: 5 givenname: Chuan-Ming surname: Yang fullname: Yang, Chuan-Ming – sequence: 6 givenname: Hong-Xi surname: Zhang fullname: Zhang, Hong-Xi – sequence: 7 givenname: Ya-Chen surname: Li fullname: Li, Ya-Chen – sequence: 8 givenname: Qiao-Ke surname: Dong fullname: Dong, Qiao-Ke – sequence: 9 givenname: Yan-Ping orcidid: 0000-0003-1666-1850 surname: Zhu fullname: Zhu, Yan-Ping – sequence: 10 givenname: Yuan-Yuan surname: Sun fullname: Sun, Yuan-Yuan |
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| Cites_doi | 10.1039/D0SC05607C 10.1021/acs.joc.8b01210 10.1021/acs.joc.9b02760 10.3390/molecules28062787 10.1039/C8OB01067F 10.1021/acs.orglett.9b00685 10.1021/acs.orglett.7b03760 10.1021/acs.orglett.0c01253 10.1039/C7SC02232H 10.1021/acs.orglett.9b03306 10.1039/D0QO00065E 10.1021/acs.orglett.9b01683 10.1039/D1SC02352G 10.1021/acs.jnatprod.2c01132 10.1002/jhet.5570190315 10.1021/acs.orglett.9b02124 10.1007/s00044-022-02958-z 10.1021/acs.joc.1c02508 10.2174/1570193X15666181029141019 10.1021/acs.orglett.9b02748 10.1021/acs.orglett.7b02885 10.1021/acs.joc.3c00206 10.1021/acs.joc.1c01982 10.1007/s00706-022-02976-y 10.1039/D0QO00855A 10.1002/asia.201901072 10.1016/j.tet.2013.09.015 10.1021/acs.orglett.2c01922 10.1021/jacs.8b03302 10.1021/jacs.3c06031 10.1021/acs.orglett.3c01579 10.1021/acscatal.2c05638 10.1021/acs.joc.1c01682 10.1021/jacs.7b02388 10.1021/acs.chemrev.0c00793 10.1016/j.chempr.2018.03.008 10.1002/anie.202011996 10.1002/asia.201600065 10.1039/C5RA00493D 10.1055/s-0036-1589155 10.1021/acs.orglett.8b01536 10.1016/j.cclet.2016.03.014 10.1021/acs.orglett.3c00636 10.1021/acscatal.3c02562 10.1039/D0QO00780C 10.1021/acs.orglett.9b01876 |
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| References | Luo (ref_7) 2020; 7 Shang (ref_40) 2021; 86 Guo (ref_5) 2018; 20 Haji (ref_9) 2022; 31 Wang (ref_16) 2023; 13 Ma (ref_41) 2017; 139 Khaligh (ref_21) 2020; 17 ref_35 Yu (ref_8) 2020; 7 Meng (ref_13) 2022; 24 Rao (ref_15) 2016; 11 Chen (ref_31) 2018; 16 Dai (ref_28) 2019; 21 Pan (ref_24) 2018; 4 Zhao (ref_36) 2019; 21 Pan (ref_18) 2021; 86 Ma (ref_33) 2021; 12 Ma (ref_29) 2021; 12 Sutariya (ref_42) 2015; 5 Dimirjian (ref_45) 2019; 21 James (ref_46) 2018; 140 Morita (ref_1) 2018; 20 Chen (ref_30) 2017; 19 Tang (ref_27) 2019; 21 Liu (ref_10) 2023; 25 Li (ref_19) 2023; 13 Jiang (ref_4) 2020; 22 Sudoh (ref_34) 1982; 19 Lin (ref_6) 2023; 88 Gao (ref_12) 2019; 21 Xiong (ref_26) 2019; 21 Jiang (ref_3) 2023; 145 Ibrahim (ref_2) 2022; 153 Zhang (ref_39) 2022; 87 Dahiya (ref_22) 2019; 14 Reyes (ref_17) 2021; 121 Osipyan (ref_11) 2018; 83 Shaikh (ref_43) 2016; 27 Guo (ref_23) 2020; 7 Song (ref_32) 2023; 25 Saidu (ref_14) 2023; 86 Choudhury (ref_38) 2017; 8 Li (ref_20) 2018; 50 Huang (ref_37) 2021; 60 Purushothaman (ref_44) 2013; 69 Wang (ref_25) 2019; 84 |
| References_xml | – volume: 12 start-page: 774 year: 2021 ident: ref_33 article-title: Acyclic nitronate olefin cycloaddition (ANOC): Regio- and stereospecific synthesis of isoxazolines publication-title: Chem. Sci. doi: 10.1039/D0SC05607C – volume: 83 start-page: 9707 year: 2018 ident: ref_11 article-title: Rare Medium-Sized Rings Prepared via Hydrolytic Imidazoline Ring Expansion (HIRE) publication-title: J. Org. Chem. doi: 10.1021/acs.joc.8b01210 – volume: 84 start-page: 16214 year: 2019 ident: ref_25 article-title: Copper-Catalyzed Cascade Cyclization Reactions of Diazo Compounds with tert-Butyl Nitrite and Alkynes: One-Pot Synthesis of Isoxazoles publication-title: J. Org. Chem. doi: 10.1021/acs.joc.9b02760 – ident: ref_35 doi: 10.3390/molecules28062787 – volume: 16 start-page: 4683 year: 2018 ident: ref_31 article-title: In situ generation of nitrile oxides from copper carbene and tert-butyl nitrite: Synthesis of fully substituted isoxazoles publication-title: Org. Biomol. Chem. doi: 10.1039/C8OB01067F – volume: 21 start-page: 2708 year: 2019 ident: ref_36 article-title: Direct Synthesis of 2,3-Diaroyl Quinolines and Pyridazino[4,5-b]quinolines via an I2-Promoted One-Pot Multicomponent Reaction publication-title: Org. Lett. doi: 10.1021/acs.orglett.9b00685 – volume: 20 start-page: 433 year: 2018 ident: ref_1 article-title: Gold(I)-Catalyzed Intramolecular SEAr Reaction: Efficienct Synthesis of Isoxazole-Containing Fused Heterocycles publication-title: Org. Lett. doi: 10.1021/acs.orglett.7b03760 – volume: 22 start-page: 4176 year: 2020 ident: ref_4 article-title: Synthetic Studies toward the Hamigerans with a 6–7–5 Tricyclic Core publication-title: Org. Lett. doi: 10.1021/acs.orglett.0c01253 – volume: 8 start-page: 6686 year: 2017 ident: ref_38 article-title: Nitro-enabled catalytic enantioselective formal umpolung alkenylation of β-ketoesters publication-title: Chem. Sci. doi: 10.1039/C7SC02232H – volume: 21 start-page: 9300 year: 2019 ident: ref_26 article-title: Synthesis of Isoxazolines and Oxazines by Electrochemical Intermolecular [2 + 1 + n] Annulation: Diazo Compounds Act as Radical Acceptors publication-title: Org. Lett. doi: 10.1021/acs.orglett.9b03306 – volume: 7 start-page: 1107 year: 2020 ident: ref_7 article-title: Toward C2-nitrogenated chromones by copper-catalyzed β-C(sp2)–H N-heteroarylation of enaminones publication-title: Org. Chem. Front. doi: 10.1039/D0QO00065E – volume: 21 start-page: 5096 year: 2019 ident: ref_28 article-title: Synthesis of 3-Acyl-isoxazoles and Δ2-Isoxazolines from Methyl Ketones, Alkynes or Alkenes, and tert-Butyl Nitrite via a Csp3–H Radical Functionalization/Cycloaddition Cascade publication-title: Org. Lett. doi: 10.1021/acs.orglett.9b01683 – volume: 12 start-page: 9823 year: 2021 ident: ref_29 article-title: [2 + 2 + 1] Cycloaddition of N-tosylhydrazones, tert-butyl nitrite and alkenes: A general and practical access to isoxazolines publication-title: Chem. Sci. doi: 10.1039/D1SC02352G – volume: 86 start-page: 891 year: 2023 ident: ref_14 article-title: Pauciflorins A–E, Unexpected Chromone–Monoterpene-Derived Meroterpenoids from Centrapalus pauciflorus publication-title: J. Nat. Prod. doi: 10.1021/acs.jnatprod.2c01132 – volume: 19 start-page: 525 year: 1982 ident: ref_34 article-title: Reactions of 3-acetyltropolone and its methyl ethers with hydroxylamine. Formation of 8H-cyclohept[d]isoxazol-8-one and 8H-cyclohept[c]isoxazol-8-one publication-title: J. Heterocycl. Chem. doi: 10.1002/jhet.5570190315 – volume: 21 start-page: 7209 year: 2019 ident: ref_45 article-title: Synthesis of Spirobicyclic Pyrazoles by Intramolecular Dipolar Cycloadditions/[1s, 5s] Sigmatropic Rearrangements publication-title: Org. Lett. doi: 10.1021/acs.orglett.9b02124 – volume: 31 start-page: 2059 year: 2022 ident: ref_9 article-title: Cyclohepta[b]pyran: An important scaffold in biologically active natural products publication-title: Med. Chem. Res. doi: 10.1007/s00044-022-02958-z – volume: 87 start-page: 835 year: 2022 ident: ref_39 article-title: Iodine-Mediated Domino Cyclization for One-Pot Synthesis of Indolizine-Fused Chromones via Metal-Free sp3 C–H Functionalization publication-title: J. Org. Chem. doi: 10.1021/acs.joc.1c02508 – volume: 17 start-page: 3 year: 2020 ident: ref_21 article-title: Recent Advances and Applications of tert-Butyl Nitrite (TBN) in Organic Synthesis publication-title: Mini-Rev. Org. Chem. doi: 10.2174/1570193X15666181029141019 – volume: 21 start-page: 7435 year: 2019 ident: ref_12 article-title: From Alkenes to Isoxazolines via Copper-Mediated Alkene Cleavage and Dipolar Cycloaddition publication-title: Org. Lett. doi: 10.1021/acs.orglett.9b02748 – volume: 19 start-page: 5896 year: 2017 ident: ref_30 article-title: Coupling Reaction of Cu-Based Carbene and Nitroso Radical: A Tandem Reaction to Construct Isoxazolines publication-title: Org. Lett. doi: 10.1021/acs.orglett.7b02885 – volume: 88 start-page: 4017 year: 2023 ident: ref_6 article-title: Cascade in Situ Iodination, Chromone Annulation, and Cyanation for Site-Selective Synthesis of 2-Cyanochromones publication-title: J. Org. Chem. doi: 10.1021/acs.joc.3c00206 – volume: 86 start-page: 16753 year: 2021 ident: ref_18 article-title: Synthesis of Indole-Fused Six-, Seven-, or Eight-Membered N,O-Heterocycles via Rhodium-Catalyzed NH-Indole-Directed C–H Acetoxylation/Hydrolysis/Annulation publication-title: J. Org. Chem. doi: 10.1021/acs.joc.1c01982 – volume: 153 start-page: 837 year: 2022 ident: ref_2 article-title: Advancements in the synthesis of oxazolines publication-title: Monatsh. Chem. doi: 10.1007/s00706-022-02976-y – volume: 7 start-page: 2770 year: 2020 ident: ref_8 article-title: Transition metal-free synthesis of 3-trifluoromethyl chromones via tandem C–H trifluoromethylation and chromone annulation of enaminones publication-title: Org. Chem. Front. doi: 10.1039/D0QO00855A – volume: 14 start-page: 4454 year: 2019 ident: ref_22 article-title: tert-Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis publication-title: Chem. Asian J. doi: 10.1002/asia.201901072 – volume: 69 start-page: 9742 year: 2013 ident: ref_44 article-title: Regioselective synthesis of spiropyrrolidine/spiropyrrolizidine/spirothiazolidine-grafted macrocycles through 1,3-dipolar cycloaddition methodology publication-title: Tetrahedron doi: 10.1016/j.tet.2013.09.015 – volume: 24 start-page: 5890 year: 2022 ident: ref_13 article-title: Synthetic and Computational Study of the Enantioselective [3 + 2]-Cycloaddition of Chromones with MBH Carbonates publication-title: Org. Lett. doi: 10.1021/acs.orglett.2c01922 – volume: 140 start-page: 8624 year: 2018 ident: ref_46 article-title: Dearomative Cascade Photocatalysis: Divergent Synthesis through Catalyst Selective Energy Transfer publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.8b03302 – volume: 145 start-page: 18731 year: 2023 ident: ref_3 article-title: Concise Total Syntheses of the 6–7–5 Hamigeran Natural Products publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.3c06031 – volume: 25 start-page: 5406 year: 2023 ident: ref_10 article-title: Construction of Indole-Fused Seven- and Eight-Membered Azaheterocycles via a Tandem Pd/NBE-Catalyzed Decarbonylation and Dual C–H Activation Sequence publication-title: Org. Lett. doi: 10.1021/acs.orglett.3c01579 – volume: 13 start-page: 1164 year: 2023 ident: ref_19 article-title: Temperature-Controlled Divergent Asymmetric Synthesis of Indole-Based Medium-Sized Heterocycles through Palladium Catalysis publication-title: ACS Catal. doi: 10.1021/acscatal.2c05638 – volume: 86 start-page: 15733 year: 2021 ident: ref_40 article-title: One-Pot Synthesis of Chromone-Fused Pyrrolo[2,1-a]isoquinolines and Indolizino[8,7-b]indoles: Iodine-Promoted Oxidative [2 + 2 + 1] Annulation of O-Acetylphenoxyacrylates with Tetrahydroisoquinolines and Noreleagnines publication-title: J. Org. Chem. doi: 10.1021/acs.joc.1c01682 – volume: 139 start-page: 5998 year: 2017 ident: ref_41 article-title: Hydroheteroarylation of Unactivated Alkenes Using N-Methoxyheteroarenium Salts publication-title: J. Am. Chem. Soc. doi: 10.1021/jacs.7b02388 – volume: 121 start-page: 8926 year: 2021 ident: ref_17 article-title: Construction of Medium-Sized Rings by Gold Catalysis publication-title: Chem. Rev. doi: 10.1021/acs.chemrev.0c00793 – volume: 4 start-page: 1427 year: 2018 ident: ref_24 article-title: Chemoselective Nitrosylation of Anilines and Alkynes via Fragmentary or Complete NO Incorporation publication-title: Chem doi: 10.1016/j.chempr.2018.03.008 – volume: 60 start-page: 2464 year: 2021 ident: ref_37 article-title: Radical Carbonyl Propargylation by Dual Catalysis publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.202011996 – volume: 11 start-page: 991 year: 2016 ident: ref_15 article-title: Ring Expansion via Cleavage of Benzylic C−C Bonds Enabling Direct Synthesis of Medium Ring-Fused Benzocarbocycles publication-title: Chem. Asian J. doi: 10.1002/asia.201600065 – volume: 5 start-page: 23519 year: 2015 ident: ref_42 article-title: A domino synthetic approach for new, angular pyrazol- and isoxazol-heterocycles using [DBU][Ac] as an effective reaction medium publication-title: RSC Adv. doi: 10.1039/C5RA00493D – volume: 50 start-page: 711 year: 2018 ident: ref_20 article-title: tert-Butyl Nitrite (TBN) as a Versatile Reagent in Organic Synthesis publication-title: Synthesis doi: 10.1055/s-0036-1589155 – volume: 20 start-page: 3971 year: 2018 ident: ref_5 article-title: Thermoinduced Free-Radical C–H Acyloxylation of Tertiary Enaminones: Catalyst-Free Synthesis of Acyloxyl Chromones and Enaminones publication-title: Org. Lett. doi: 10.1021/acs.orglett.8b01536 – volume: 27 start-page: 1058 year: 2016 ident: ref_43 article-title: 1,2,3-Triazole tethered acetophenones: Synthesis, bioevaluation and molecular docking study publication-title: Chin. Chem. Lett. doi: 10.1016/j.cclet.2016.03.014 – volume: 25 start-page: 2139 year: 2023 ident: ref_32 article-title: Tunable Key [3 + 2] and [2 + 1] Cycloaddition of Enaminones and α-Diazo Compounds for the Synthesis of Isomeric Isoxazoles: Metal-Controlled Selectivity publication-title: Org. Lett. doi: 10.1021/acs.orglett.3c00636 – volume: 13 start-page: 10694 year: 2023 ident: ref_16 article-title: Catalyst-Controlled Switchable (5 + 4)/(3 + 4) Cycloadditions for the Divergent Synthesis of Pyrazole-Fused Seven- and Nine-Membered Heterocycles publication-title: ACS Catal. doi: 10.1021/acscatal.3c02562 – volume: 7 start-page: 2467 year: 2020 ident: ref_23 article-title: Synthesis and application of α-carbonyl nitrile oxides publication-title: Org. Chem. Front. doi: 10.1039/D0QO00780C – volume: 21 start-page: 5273 year: 2019 ident: ref_27 article-title: Synthesis of Furoxans and Isoxazoles via Divergent [2 + 1 + 1 + 1] Annulations of Sulfoxonium Ylides and tBuONO publication-title: Org. Lett. doi: 10.1021/acs.orglett.9b01876 |
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| SubjectTerms | aryl methyl ketones Chemical bonds Chromatography intramolecular cycloaddition Investigations isoxazole/isoxazoline Natural products Oxidation polycyclic architectures tert-butyl nitrite (TBN) |
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| Title | tert-Butyl Nitrite-Induced Radical Nitrile Oxidation Cycloaddition: Synthesis of Isoxazole/Isoxazoline-Fused Benzo 6/7/8-membered Oxacyclic Ketones |
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