Intermolecular one-pot cyclization of formyl-pyrroles of amino acid esters with norephedrine: stereoselective routes to new tricyclic pyrrole–pyrazine–oxazole fused structures期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

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Intermolecular one-pot cyclization of formyl-pyrroles of amino acid esters with norephedrine: stereoselective routes to new tricyclic pyrrole–pyrazine–oxazole fused structures

Institution:	1. Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey;2. Department of Chemistry, Faculty of Arts and Sciences, Atatürk University, 25240 Erzurum, Turkey;1. Department of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, Saint Petersburg, 198504 Russian Federation;2. A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation;1. Department of Chemical Engineering, Faculty of Engineering and Architecture, Ahi Evran University, 40100, Kırşehir, Turkey;2. Department of Chemistry, Faculty of Science, Firat University, 23119, Elazig, Turkey;3. Department of Food Engineering, Faculty of Engineering and Architecture, Ahi Evran University, 40100, Kırşehir, Turkey;4. Department of Chemistry, Faculty of Science, Anadolu University, 26470, Eskişehir, Turkey;1. Department of Chemistry, Faculty of Science, Taibah University, P.O. Box 30002, Al-Madinah Al-Munawarah, Saudi Arabia;2. Organic Structural Chemistry Laboratory, Synthesis and Physico-Chemical Studies, Chemistry Department, Faculty of Science of Tunis, University of Tunis El Manar, 2092 Tunis, Tunisia;1. Institute of Polymer Materials, School of Materials Science and Engineering, Jiangsu University, Zhenjiang, China;2. Institute of Green Chemistry and Chemical Technology, Jiangsu University, Zhenjiang, China

Abstract:	The treatment of esters of amino acids with dimethoxytetrahydrofuran furnished pyrrole derivatives of amino acid esters. The Wilsmeier–Haack formylation followed by the reaction of the formylated pyrroles with norephedrine afforded a selective formation of the tricyclic pyrrole–pyrazine–oxazole fused structures in one step via the formation of an oxazoline structure and intramolecular lactam formation. Pyrrole–pyrazine–oxazole fused structures were achieved in good yields. The cyclization reaction for the formation of an oxazole ring worked selectively to form only one stereoisomer. The configuration of the newly generated stereogenic center in the oxazole ring is dependent on the stereogenic centers of norephedrine.

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