دورية أكاديمية

Rh(III)-Catalyzed Imidoyl C-H Carbamylation and Cyclization to Bicyclic [1,3,5]Triazinones.

التفاصيل البيبلوغرافية
العنوان: Rh(III)-Catalyzed Imidoyl C-H Carbamylation and Cyclization to Bicyclic [1,3,5]Triazinones.
المؤلفون: Confair DN; Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States., Greenwood NS; Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States., Mercado BQ; Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States., Ellman JA; Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
المصدر: Organic letters [Org Lett] 2020 Nov 20; Vol. 22 (22), pp. 8993-8997. Date of Electronic Publication: 2020 Nov 10.
نوع المنشور: Journal Article; Research Support, N.I.H., Extramural
اللغة: English
بيانات الدورية: Publisher: American Chemical Society Country of Publication: United States NLM ID: 100890393 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1523-7052 (Electronic) Linking ISSN: 15237052 NLM ISO Abbreviation: Org Lett Subsets: MEDLINE
أسماء مطبوعة: Original Publication: Washington, DC : American Chemical Society, c1999-
مواضيع طبية MeSH: Imines/*chemistry , Rhodium/*chemistry , Triazines/*chemistry, Catalysis ; Cyclization ; Molecular Structure ; Protein Carbamylation
مستخلص: A Rh(III)-catalyzed synthesis of bicyclic [1,3,5]triazinones from a diverse array of imines coupled with ethyl (pivaloyloxy)carbamate is reported. The preparation of [5,6]- and [6,6]-bicyclic heterocycles substituted with aryl, alkyl, and alkoxy groups demonstrated a broad reaction scope. The efficiency of this approach was further enhanced with the development of a three-component variant featuring in situ imine formation. X-ray crystallographic characterization of a rhodacycle formed by imidoyl C-H activation provides support for the proposed mechanism.
References: Org Lett. 2019 Jun 7;21(11):3886-3890. (PMID: 30896175)
Org Lett. 2020 Feb 7;22(3):1217-1221. (PMID: 31977232)
Chem Rev. 2017 Jul 12;117(13):9247-9301. (PMID: 28051855)
Org Lett. 2018 Apr 20;20(8):2464-2467. (PMID: 29582661)
J Am Chem Soc. 2012 Jan 25;134(3):1482-5. (PMID: 22257031)
Angew Chem Int Ed Engl. 2011 Nov 11;50(46):10917-21. (PMID: 21922622)
J Org Chem. 2018 Dec 21;83(24):15347-15360. (PMID: 30525637)
Org Biomol Chem. 2017 May 16;15(19):4064-4067. (PMID: 28443919)
J Org Chem. 2018 Aug 17;83(16):9522-9529. (PMID: 29947517)
Chemistry. 2015 Nov 23;21(48):17200-4. (PMID: 26463666)
Org Lett. 2020 Jul 17;22(14):5706-5711. (PMID: 32638595)
Org Lett. 2013 Jun 21;15(12):3014-7. (PMID: 23724964)
Org Lett. 2019 Mar 1;21(5):1273-1277. (PMID: 30747539)
J Am Chem Soc. 2012 Jun 6;134(22):9110-3. (PMID: 22624801)
Org Lett. 2014 Jun 20;16(12):3328-31. (PMID: 24901257)
معلومات مُعتمدة: R35 GM122473 United States GM NIGMS NIH HHS
المشرفين على المادة: 0 (Imines)
0 (Triazines)
DMK383DSAC (Rhodium)
تواريخ الأحداث: Date Created: 20201111 Date Completed: 20210810 Latest Revision: 20211121
رمز التحديث: 20231215
مُعرف محوري في PubMed: PMC7702018
DOI: 10.1021/acs.orglett.0c03393
PMID: 33172274
قاعدة البيانات: MEDLINE
الوصف
تدمد:1523-7052
DOI:10.1021/acs.orglett.0c03393