دورية أكاديمية
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Nitro-sulfinate Reductive Coupling to Access (Hetero)aryl Sulfonamides.

التفاصيل البيبلوغرافية
العنوان: Nitro-sulfinate Reductive Coupling to Access (Hetero)aryl Sulfonamides.
المؤلفون: Gatarz SE; Yusuf Hamied Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, U.K., Griffiths OM; Yusuf Hamied Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, U.K., Esteves HA; Yusuf Hamied Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, U.K., Jiao W; Yusuf Hamied Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, U.K., Morse P; Medicine Design, Pfizer, Inc., Groton, Connecticut 06340, United States., Fisher EL; Medicine Design, Pfizer, Inc., Groton, Connecticut 06340, United States., Blakemore DC; Medicine Design, Pfizer, Inc., Groton, Connecticut 06340, United States., Ley SV; Yusuf Hamied Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, U.K.
المصدر: The Journal of organic chemistry [J Org Chem] 2024 Feb 02; Vol. 89 (3), pp. 1898-1909. Date of Electronic Publication: 2024 Jan 18.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: American Chemical Society Country of Publication: United States NLM ID: 2985193R Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-6904 (Electronic) Linking ISSN: 00223263 NLM ISO Abbreviation: J Org Chem Subsets: PubMed not MEDLINE; MEDLINE
أسماء مطبوعة: Publication: Columbus Oh : American Chemical Society
Original Publication: Easton, Pa. [etc.]
مستخلص: A method to assemble (hetero)aryl sulfonamides via the reductive coupling of aryl sulfinates and nitroarenes is reported. Various reducing conditions with sodium bisulfite and with or without tin(II) chloride in DMSO were developed using an ultrasound bath to improve reaction homogeneity and mixing. A range of (hetero)aryl sulfonamides bearing a selection of functional groups were prepared, and the mechanism of the transformation was investigated. These investigations have led us to propose the formation of nitrosoarene intermediates, which were established via an independent molecular coupling strategy.
References: Chem Commun (Camb). 2013 Jun 25;49(50):5654-6. (PMID: 23677037)
Eur J Med Chem. 2019 Jan 15;162:679-734. (PMID: 30496988)
Chem Rev. 2016 Jan 13;116(1):258-86. (PMID: 26730505)
Molecules. 2019 Apr 10;24(7):. (PMID: 30974790)
Org Lett. 2011 Jan 7;13(1):102-5. (PMID: 21126054)
Org Lett. 2021 Apr 2;23(7):2797-2801. (PMID: 33719466)
Chem Commun (Camb). 2013 Jul 11;49(54):6102-4. (PMID: 23730689)
Angew Chem Int Ed Engl. 2012 Jun 25;51(26):6502-5. (PMID: 22644884)
Top Curr Chem (Cham). 2018 Jan 22;376(1):5. (PMID: 29356979)
Org Lett. 2003 Nov 13;5(23):4373-6. (PMID: 14602003)
Angew Chem Int Ed Engl. 2018 Mar 19;57(13):3488-3492. (PMID: 29424956)
Expert Opin Drug Discov. 2021 Jul;16(7):723-726. (PMID: 33769176)
Expert Opin Drug Discov. 2019 Apr;14(4):335-341. (PMID: 30806519)
J Am Chem Soc. 2018 Jul 18;140(28):8781-8787. (PMID: 29965736)
Chem Commun (Camb). 2013 Jun 7;49(45):5225-7. (PMID: 23628894)
Org Biomol Chem. 2018 Jul 11;16(27):5016-5020. (PMID: 29946613)
Curr Opin Drug Discov Devel. 2008 Jan;11(1):72-9. (PMID: 18175269)
J Org Chem. 2011 Jun 3;76(11):4552-63. (PMID: 21510695)
Chem Commun (Camb). 2020 Mar 19;56(23):3437-3440. (PMID: 32100803)
Org Biomol Chem. 2018 Nov 7;16(43):8150-8154. (PMID: 30335119)
J Am Chem Soc. 2013 Jul 24;135(29):10638-41. (PMID: 23837740)
Chem Sci. 2022 Dec 15;14(3):525-532. (PMID: 36741536)
Org Lett. 2011 May 20;13(10):2564-7. (PMID: 21510692)
Org Lett. 2020 Mar 6;22(5):1841-1845. (PMID: 32073282)
J Am Chem Soc. 2004 Feb 4;126(4):1024-5. (PMID: 14746462)
Chem Rev. 2014 Feb 26;114(4):2507-86. (PMID: 24341435)
Beilstein J Org Chem. 2013 May 31;9:1051-72. (PMID: 23766820)
Org Biomol Chem. 2022 Apr 13;20(15):3154-3159. (PMID: 35343994)
Chem Commun (Camb). 2005 Jul 28;(28):3514-25. (PMID: 16010311)
Org Lett. 2010 Apr 2;12(7):1532-5. (PMID: 20196553)
J Org Chem. 2006 Feb 3;71(3):1080-4. (PMID: 16438524)
J Org Chem. 2015 Apr 3;80(7):3504-11. (PMID: 25742395)
RSC Adv. 2021 Mar 1;11(16):9130-9221. (PMID: 35423435)
J Am Chem Soc. 2023 Oct 4;145(39):21189-21196. (PMID: 37729614)
Bioorg Med Chem. 2020 Jan 1;28(1):115186. (PMID: 31759826)
Angew Chem Int Ed Engl. 2011 Nov 11;50(46):10800-26. (PMID: 22038946)
J Org Chem. 2009 Dec 18;74(24):9287-91. (PMID: 19919028)
J Nat Prod. 2018 Feb 23;81(2):423-446. (PMID: 29364663)
Carcinogenesis. 2010 Jan;31(1):50-8. (PMID: 19887514)
تواريخ الأحداث: Date Created: 20240119 Latest Revision: 20240210
رمز التحديث: 20240210
مُعرف محوري في PubMed: PMC10845164
DOI: 10.1021/acs.joc.3c02557
PMID: 38239107
قاعدة البيانات: MEDLINE
الوصف
تدمد:1520-6904
DOI:10.1021/acs.joc.3c02557