دورية أكاديمية
Base-Mediated, Chemo- and Regioselective (4+2) Annulation of Indole-2-carboxamides with 2,3-Epoxy Tosylates toward 1,2-Fused Indoles.
| العنوان: | Base-Mediated, Chemo- and Regioselective (4+2) Annulation of Indole-2-carboxamides with 2,3-Epoxy Tosylates toward 1,2-Fused Indoles. |
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| المؤلفون: | Das AJ; Department of Chemical Sciences, Tezpur University, Napaam, Sonitpur, Assam 784028, India., Das SK; Department of Chemical Sciences, Tezpur University, Napaam, Sonitpur, Assam 784028, India. |
| المصدر: | The Journal of organic chemistry [J Org Chem] 2023 Jul 07; Vol. 88 (13), pp. 9237-9248. Date of Electronic Publication: 2023 Jun 08. |
| 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.] |
| مواضيع طبية MeSH: | Indoles* , Epoxy Compounds*, Cyclization |
| مستخلص: | Base-mediated [4+2] annulation of indole-2-carboxamides with 2,3-epoxy tosylates has been explored. The protocol delivers 3-substituted pyrazino[1,2- a ]indol-1-ones in high yields in diastereoselective fashion, and neither 4-substituted pyrazino[1,2- a ]indol-1-ones nor tetrahydro-1 H -[1,4]diazepino[1,2- a ]indol-1-ones are generated, irrespective of whether the distal epoxide C3 substituent is alkyl or aryl, or the epoxide is cis - or trans -configured. This reaction proceeds in one pot via N-alkylation of the indole scaffold with 2,3-epoxy tosylates, concomitantly followed by 6-exo-selective epoxide-opening cyclization. Notably, the process is chemo- and regioselective with respect to both the starting materials. To our knowledge, the process represents the first successful example of one-pot annulation of indole-based diheteronucleophiles with epoxide-based dielectrophiles. |
| المشرفين على المادة: | 8724FJW4M5 (indole) 0 (Indoles) 0 (Epoxy Compounds) |
| تواريخ الأحداث: | Date Created: 20230608 Date Completed: 20230710 Latest Revision: 20230718 |
| رمز التحديث: | 20240628 |
| DOI: | 10.1021/acs.joc.3c00813 |
| PMID: | 37289967 |
| قاعدة البيانات: | MEDLINE |
Find this issue from the American Chemical Society | تدمد: | 1520-6904 |
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| DOI: | 10.1021/acs.joc.3c00813 |