دورية أكاديمية
Chiral pyridin-3-ones and pyridines: syntheses of enantiopure 2,4-disubstituted 6-hydroxy-1,6-dihydro-2H-pyridin-3-ones, 2,3-disubstituted 4-iodopyridines, and enantiopure 2,3-disubstituted 4-pyridinemethanols.
| العنوان: | Chiral pyridin-3-ones and pyridines: syntheses of enantiopure 2,4-disubstituted 6-hydroxy-1,6-dihydro-2H-pyridin-3-ones, 2,3-disubstituted 4-iodopyridines, and enantiopure 2,3-disubstituted 4-pyridinemethanols. |
|---|---|
| المؤلفون: | Husain I; Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, PO Box 173, Lucknow-226001, India., Saquib M, Bajpai V, Kumar B, Shaw AK |
| المصدر: | The Journal of organic chemistry [J Org Chem] 2011 Nov 04; Vol. 76 (21), pp. 8930-43. Date of Electronic Publication: 2011 Oct 05. |
| نوع المنشور: | Journal Article; Research Support, Non-U.S. Gov't |
| 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: MEDLINE |
| أسماء مطبوعة: | Publication: Columbus Oh : American Chemical Society Original Publication: Easton, Pa. [etc.] |
| مواضيع طبية MeSH: | Iodopyridones/*chemical synthesis , Iodopyridones/*chemistry , Pyridines/*chemical synthesis , Pyridines/*chemistry , Pyridones/*chemical synthesis , Pyridones/*chemistry, Molecular Structure ; Stereoisomerism |
| مستخلص: | The development of an innovative method to access enantiopure 2,4-disubstituted 6-hydroxy-1,6-dihydro-2H-pyridin-3-ones starting from D-glucal via the aza-Achmatowicz transformation has been described. These highly functionalized pyridin-3-ones have been utilized for the synthesis of contiguously substituted pyridines through a rapid and efficient Et(3)N/Ac(2)O promoted cyclo-elimination, aromatization cascade, allowing the facile assembly of important pyridine-based building blocks like 2-substituted 3-acetoxy-4-iodopyridines and enantiopure 2-substituted 3-acetoxy-4-pyridinemethanols possessing benzylic stereogenic centers, whose synthesis otherwise would be tedious. The utilization of commercially available sugars as starting materials, mild reaction conditions, catalytic transfer hydrogen (CTH) of α-furfuryl azide derivatives, transfer of chiral aryl/alkyl methanols from enulosides to pyridin-3-ones and pyridines, high yields, and short reaction times are key features of this method. The utility of the method has been further exemplified by demonstrating the usage of the 2-substituted 3-acetoxy-4-iodopyridine for the construction of biologically significant molecules like 2,7-disubstituted furo[2,3-c]pyridines and 7,7'-disubstituted 2,2'-bifuro[2,3-c]pyridines. |
| المشرفين على المادة: | 0 (Iodopyridones) 0 (Pyridines) 0 (Pyridones) |
| تواريخ الأحداث: | Date Created: 20110930 Date Completed: 20120313 Latest Revision: 20111028 |
| رمز التحديث: | 20221213 |
| DOI: | 10.1021/jo201662n |
| PMID: | 21955144 |
| قاعدة البيانات: | MEDLINE |
Find this issue from the American Chemical Society | تدمد: | 1520-6904 |
|---|---|
| DOI: | 10.1021/jo201662n |