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Literature DB >> 20184347

Synthesis of benzisoxazoles by the [3 + 2] cycloaddition of in situ generated nitrile oxides and arynes.

Abstract

A variety of substituted benzisoxazoles has been prepared by the [3 + 2] cycloaddition of nitrile oxides and arynes. Both components, being highly reactive intermediates, have been generated in situ by fluoride anion from readily prepared aryne precursors and chlorooximes. The reaction scope is quite general, affording a novel, direct route to functionalized benzisoxazoles under mild reaction conditions.

Entities: Chemical Disease Gene

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Year: 2010 PMID： 20184347 PMCID： PMC2852127 DOI： 10.1021/ol902921s

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

13 in total

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Authors: J T Strupczewski; K J Bordeau; Y Chiang; E J Glamkowski; P G Conway; R Corbett; H B Hartman; M R Szewczak; C A Wilmot; G C Helsley
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Journal: Bioorg Med Chem Lett Date: 2003-05-19 Impact factor: 2.823

4. Benzyne click chemistry: synthesis of benzotriazoles from benzynes and azides.

Authors: Feng Shi; Jesse P Waldo; Yu Chen; Richard C Larock
Journal: Org Lett Date: 2008-05-14 Impact factor: 6.005

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Authors: Ariamala Gopalsamy; Mengxiao Shi; Jennifer Golas; Erik Vogan; Jaison Jacob; Mark Johnson; Frederick Lee; Ramaswamy Nilakantan; Roseann Petersen; Kristin Svenson; Rajiv Chopra; May S Tam; Yingxia Wen; John Ellingboe; Kim Arndt; Frank Boschelli
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7. Pharmacology of risperidone (R 64 766), a new antipsychotic with serotonin-S2 and dopamine-D2 antagonistic properties.

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8. Novel benzisoxazole derivatives as potent and selective inhibitors of acetylcholinesterase.

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Journal: J Med Chem Date: 1994-08-19 Impact factor: 7.446

9. Studies of nitrile oxide cycloadditions, and the phenolic oxidative coupling of vanillin aldoxime by Geobacillus sp. DDS012 from Italian rye grass silage.

Authors: David R Kelly; Simon C Baker; David S King; Deepa S de Silva; Gwyn Lord; Jason P Taylor
Journal: Org Biomol Chem Date: 2008-01-21 Impact factor: 3.876

10. 1,2-benzisoxazole phosphorodiamidates as novel anticancer prodrugs requiring bioreductive activation.

Authors: Monish Jain; Chul-Hoon Kwon
Journal: J Med Chem Date: 2003-12-04 Impact factor: 7.446

13 in total

1. Metal-free sequential [3 + 2]-dipolar cycloadditions using cyclooctynes and 1,3-dipoles of different reactivity.

Authors: Brian C Sanders; Frédéric Friscourt; Petr A Ledin; Ngalle Eric Mbua; Selvanathan Arumugam; Jun Guo; Thomas J Boltje; Vladimir V Popik; Geert-Jan Boons
Journal: J Am Chem Soc Date: 2010-12-23 Impact factor: 15.419

2. Synthesis of spiro-fused pyrazolidoylisoxazolines.

Authors: Kathryn G Guggenheim; Jeffrey D Butler; Phillip P Painter; Beth A Lorsbach; Dean J Tantillo; Mark J Kurth
Journal: J Org Chem Date: 2011-06-22 Impact factor: 4.354

3. Synthesis of 2H-indazoles by the [3 + 2] cycloaddition of arynes and sydnones.

Authors: Chunrui Wu; Yuesi Fang; Richard C Larock; Feng Shi
Journal: Org Lett Date: 2010-05-21 Impact factor: 6.005

4. Intermolecular C-O addition of carboxylic acids to arynes.

Authors: Anton V Dubrovskiy; Richard C Larock
Journal: Org Lett Date: 2010-07-16 Impact factor: 6.005

5. Synthesis of 2H-indazoles by the [3 + 2] dipolar cycloaddition of sydnones with arynes.

Authors: Yuesi Fang; Chunrui Wu; Richard C Larock; Feng Shi
Journal: J Org Chem Date: 2011-10-12 Impact factor: 4.354

6. Synthesis of dihydrobenzisoxazoles by the [3 + 2] cycloaddition of arynes and oxaziridines.

Authors: Arif Kivrak; Richard C Larock
Journal: J Org Chem Date: 2010-11-05 Impact factor: 4.354

7. Synthesis of benzisoxazolines by the coupling of arynes with nitrones.

Authors: Chun Lu; Anton V Dubrovskiy; Richard C Larock
Journal: J Org Chem Date: 2012-02-16 Impact factor: 4.354

8. Intermolecular C-O Addition of Carboxylic Acids to Arynes: Synthesis of o-Hydroxyaryl Ketones, Xanthones, 4-Chromanones, and Flavones.

Authors: Anton V Dubrovskiy; Richard C Larock
Journal: Tetrahedron Date: 2013-02-04 Impact factor: 2.457

9. Solution-phase synthesis of a diverse library of benzisoxazoles utilizing the [3 + 2] cycloaddition of in situ-generated nitrile oxides and arynes.

Authors: Anton V Dubrovskiy; Prashi Jain; Feng Shi; Gerald H Lushington; Conrad Santini; Patrick Porubsky; Richard C Larock
Journal: ACS Comb Sci Date: 2013-03-08 Impact factor: 3.784

10. 1,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles.

Authors: Takashi Ikawa; Shigeaki Masuda; Akira Takagi; Shuji Akai
Journal: Chem Sci Date: 2016-04-18 Impact factor: 9.825