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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   
Yazarlar
Ayhan S Demir
Dr. Öğr. Üyesi Nuriye Tuna SUBAŞI Dr. Öğr. Üyesi Nuriye Tuna SUBAŞI
Ahi Evran Üniversitesi, Türkiye
Ertan Şahin
Türkiye
Özet
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. (c) 2006 Elsevier Ltd. All rights reserved.
Anahtar Kelimeler
Makale Türü Özgün Makale
Makale Alt Türü SSCI, AHCI, SCI, SCI-Exp dergilerinde yayımlanan tam makale
Dergi Adı TETRAHEDRON-ASYMMETRY
Dergi ISSN 0957-4166
Dergi Tarandığı Indeksler SCI-Expanded
Makale Dili İngilizce
Basım Tarihi 10-2006
Cilt No 17
Sayı 18
Sayfalar 2625 / 2631
Doi Numarası 10.1016/j.tetasy.2006.09.020
Makale Linki http://dx.doi.org/10.1016/j.tetasy.2006.09.020