کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5222812 1383466 2009 7 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
An annulation method for the synthesis of alkyl-substituted 6-carbomethoxy-2-pyridones
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
An annulation method for the synthesis of alkyl-substituted 6-carbomethoxy-2-pyridones
چکیده انگلیسی

A protocol for the synthesis of 5-alkyl and 3,5-dialkyl-6-carbomethoxy-2-pyridones was devised. Key steps include a Mannich reaction, acylation of a tosylamine, and a PPh3/TiCl4-promoted intramolecular Reformatsky-type reaction with a thioester as the electrophile. The latter process typically afforded a vinylogous thiocarbamate via elimination of water rather than the Dieckmann-type product which would have resulted from elimination of the thiol. However, the Dieckmann-type ketone product was obtained in one instance. Subsequent elimination of the tosyl group and desulfurization completed the pyridone synthesis.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 65, Issue 33, 15 August 2009, Pages 6584-6590
نویسندگان
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