دورية أكاديمية
α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2- a ]quinoxalines, quinazolinones, and other N-heterocycles via decarboxylative oxidative annulation reaction.
العنوان: | α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2- a ]quinoxalines, quinazolinones, and other N-heterocycles via decarboxylative oxidative annulation reaction. |
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المؤلفون: | Viji M; College of Pharmacy, Medicinal Research Center (MRC), Chungbuk National University Cheongju 28160 Republic of Korea orgjkjung@chungbuk.ac.kr +82-43-268-2732 +82-43-261-2635., Vishwanath M; College of Pharmacy, Medicinal Research Center (MRC), Chungbuk National University Cheongju 28160 Republic of Korea orgjkjung@chungbuk.ac.kr +82-43-268-2732 +82-43-261-2635., Sim J; College of Pharmacy, Medicinal Research Center (MRC), Chungbuk National University Cheongju 28160 Republic of Korea orgjkjung@chungbuk.ac.kr +82-43-268-2732 +82-43-261-2635., Park Y; College of Pharmacy, Medicinal Research Center (MRC), Chungbuk National University Cheongju 28160 Republic of Korea orgjkjung@chungbuk.ac.kr +82-43-268-2732 +82-43-261-2635., Jung C; College of Pharmacy, Medicinal Research Center (MRC), Chungbuk National University Cheongju 28160 Republic of Korea orgjkjung@chungbuk.ac.kr +82-43-268-2732 +82-43-261-2635., Lee S; College of Pharmacy, Medicinal Research Center (MRC), Chungbuk National University Cheongju 28160 Republic of Korea orgjkjung@chungbuk.ac.kr +82-43-268-2732 +82-43-261-2635., Lee H; College of Pharmacy, Medicinal Research Center (MRC), Chungbuk National University Cheongju 28160 Republic of Korea orgjkjung@chungbuk.ac.kr +82-43-268-2732 +82-43-261-2635., Lee K; College of Pharmacy, Korea University Sejong 30019 Republic of Korea., Jung JK; College of Pharmacy, Medicinal Research Center (MRC), Chungbuk National University Cheongju 28160 Republic of Korea orgjkjung@chungbuk.ac.kr +82-43-268-2732 +82-43-261-2635. |
المصدر: | RSC advances [RSC Adv] 2020 Oct 07; Vol. 10 (61), pp. 37202-37208. Date of Electronic Publication: 2020 Oct 07 (Print Publication: 2020). |
نوع المنشور: | Journal Article |
اللغة: | English |
بيانات الدورية: | Publisher: Royal Society of Chemistry Country of Publication: England NLM ID: 101581657 Publication Model: eCollection Cited Medium: Internet ISSN: 2046-2069 (Electronic) Linking ISSN: 20462069 NLM ISO Abbreviation: RSC Adv Subsets: PubMed not MEDLINE |
أسماء مطبوعة: | Original Publication: Cambridge [England] : Royal Society of Chemistry, [2011]- |
مستخلص: | A metal-free and efficient procedure for the synthesis of pyrrolo[1,2- a ]quinoxalines, quinazolinones, and indolo[1,2- a ]quinoxaline has been developed. The key features of our method include the in situ generation of aldehyde from α-hydroxy acid in the presence of TBHP ( tert -butyl hydrogen peroxide), and further condensation with various amines, followed by intramolecular cyclization and subsequent oxidation to afford the corresponding quinoxalines, quinazolinones derivatives in moderate to high yields. Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.) |
References: | Org Lett. 2012 Feb 17;14(4):1150-3. (PMID: 22313025) Eur J Med Chem. 2019 May 15;170:157-172. (PMID: 30884322) J Org Chem. 2019 Aug 2;84(15):9661-9670. (PMID: 31267751) J Am Chem Soc. 2018 Feb 28;140(8):2765-2768. (PMID: 29389123) J Enzyme Inhib Med Chem. 2008 Oct;23(5):648-58. (PMID: 18821254) Biochemistry. 2005 Jul 19;44(28):9637-44. (PMID: 16008349) Chem Commun (Camb). 2019 Mar 21;55(25):3606-3609. (PMID: 30843908) ACS Comb Sci. 2011 May 9;13(3):209-13. (PMID: 21488625) Molecules. 2019 Oct 21;24(20):. (PMID: 31640238) J Org Chem. 2017 Aug 4;82(15):8058-8066. (PMID: 28721733) Org Lett. 2019 Apr 19;21(8):2855-2858. (PMID: 30933523) Eur J Med Chem. 2019 Apr 15;168:146-153. (PMID: 30818175) Phytochemistry. 2003 Sep;64(2):609-15. (PMID: 12943784) J Org Chem. 2020 Jun 5;85(11):7378-7385. (PMID: 32400159) Chem Commun (Camb). 2017 Oct 19;53(84):11572-11575. (PMID: 28990598) Org Lett. 2019 Oct 18;21(20):8395-8399. (PMID: 31580083) Org Lett. 2019 Jun 21;21(12):4725-4728. (PMID: 31184195) J Org Chem. 2017 Jan 6;82(1):765-769. (PMID: 28056510) J Am Chem Soc. 2005 Dec 7;127(48):17000-6. (PMID: 16316246) Chemistry. 2019 Nov 18;25(64):14506-14511. (PMID: 31353634) Eur J Med Chem. 2013 Jul;65:205-22. (PMID: 23711832) Org Lett. 2012 Sep 21;14(18):4754-7. (PMID: 22971137) J Org Chem. 2019 Jun 7;84(11):6737-6751. (PMID: 31050290) Org Biomol Chem. 2011 Nov 7;9(21):7351-7. (PMID: 21894335) Org Biomol Chem. 2018 Jun 20;16(24):4482-4494. (PMID: 29869668) Org Biomol Chem. 2016 Sep 14;14(34):8014-25. (PMID: 27477737) Org Lett. 2013 Mar 1;15(5):1140-3. (PMID: 23427905) J Am Chem Soc. 2010 Jan 20;132(2):686-93. (PMID: 20000840) Biomolecules. 2020 Feb 27;10(3):. (PMID: 32120929) ChemSusChem. 2019 Jul 5;12(13):3043-3048. (PMID: 30791215) Free Radic Biol Med. 2020 Feb 20;148:33-41. (PMID: 31874248) Org Lett. 2017 Oct 6;19(19):5470-5473. (PMID: 28952319) Org Biomol Chem. 2017 Aug 30;15(34):7157-7164. (PMID: 28805833) Chem Rev. 2011 Mar 9;111(3):1846-913. (PMID: 21235271) J Enzyme Inhib Med Chem. 2010 Apr;25(2):204-15. (PMID: 20222763) Eur J Med Chem. 2011 Jun;46(6):2310-26. (PMID: 21458112) Org Biomol Chem. 2015 Sep 28;13(36):9336-52. (PMID: 26278395) Chemistry. 2020 Mar 9;26(14):3026-3029. (PMID: 31922300) Org Lett. 2015 Jun 19;17(12):2932-5. (PMID: 26052923) J Org Chem. 2015 Jul 17;80(14):7099-107. (PMID: 26098660) J Org Chem. 2015 Jul 2;80(13):6875-84. (PMID: 26057737) Chem Asian J. 2019 Aug 16;14(16):2898-2902. (PMID: 31283108) Org Lett. 2019 Jun 21;21(12):4734-4738. (PMID: 31190545) Org Lett. 2018 Nov 16;20(22):7095-7099. (PMID: 30388020) Chem Commun (Camb). 2019 Dec 7;55(94):14170-14173. (PMID: 31701971) J Org Chem. 2019 Aug 16;84(16):10160-10171. (PMID: 31327228) Eur J Med Chem. 2015 Jan 27;90:124-69. (PMID: 25461317) Bioorg Med Chem. 2019 Feb 1;27(3):568-577. (PMID: 30600149) Mol Pharmacol. 2015 Aug;88(2):401-20. (PMID: 26056160) Org Lett. 2013 Dec 6;15(23):5990-3. (PMID: 24251373) Chem Commun (Camb). 2008 Dec 14;(46):6215-7. (PMID: 19082124) Nat Commun. 2019 Apr 12;10(1):1699. (PMID: 30979892) Org Lett. 2019 May 3;21(9):3337-3341. (PMID: 31002524) Chem Commun (Camb). 2012 May 4;48(35):4253-5. (PMID: 22441208) J Med Chem. 2004 Apr 8;47(8):1997-2009. (PMID: 15055999) Org Biomol Chem. 2016 Nov 22;14(46):10763-10777. (PMID: 27805211) ACS Omega. 2019 May 07;4(5):8207-8213. (PMID: 31459909) J Org Chem. 2018 Oct 5;83(19):11747-11757. (PMID: 30148633) Bioorg Med Chem. 2016 Jun 1;24(11):2361-81. (PMID: 27112448) Sci Rep. 2020 Feb 5;10(1):1863. (PMID: 32024909) Org Biomol Chem. 2019 Sep 21;17(35):8067-8070. (PMID: 31451812) |
تواريخ الأحداث: | Date Created: 20220506 Latest Revision: 20220716 |
رمز التحديث: | 20231215 |
مُعرف محوري في PubMed: | PMC9057147 |
DOI: | 10.1039/d0ra07093a |
PMID: | 35521290 |
قاعدة البيانات: | MEDLINE |
تدمد: | 2046-2069 |
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DOI: | 10.1039/d0ra07093a |