Yeni Oksazolidintiyonların Sentezi ve Halka Açma Tepkimeleri

Year 2011, Issue: 1, 15 - 26, 01.01.2011

Nezire Saygılı

Abstract

Homokiral ve rasemik b-amino alkollerin 4a-e tiyofosgen ile etkileştirilmesinden beş yeni oksazolidintiyon 5a-e sentezlendi. 5a-e bileşiklerinin, beş yeni oksazolidintiyon 6a-e molekülü oluşturacak şekilde di-tert-butil dikarbonat boc 2O ile korunumları gerçekleştirildi. 6d ve 6e oksazolidintiyon heterosiklik yapılarının 5-C pozisyonunda halka açma tepkimeleri, karşılık gelen N-boc korunumlu esterleri 7d-f verdi. Reaksiyonların stereomerkeze bağlı hiçbir bağın kırılmadığı tarzda gerçekleşmesi nedeniyle, sentezlerdeki tüm tepkimelerin stereokimyası ‘S’ konfigürasyonun korunumuyla gerçekleşmiştir. Sentezlenmiş bileşiklerin yapıları 1H NMR, 13C NMR, IR ve MS spektral verilerle karakterize edildi.

Keywords

Oksazolidinonlar, oksazolidintiyonlar, sentez

Synthesis of New Oxazolidinethiones and Their Ring Opening Reactions

Abstract

Five new oxazolidinethiones 5a-e were synthesized from the treatment of homochiral and racemic b-amino alcohols 4a-e with thiophosgene. Compounds 5a-e was protected with di-tert-butyl dicarbonate boc 2O to afford five new N-boc protected oxazolidinethiones 6a-e . The ring opening reactions of 6d and 6e at 5-C position of the oxazolidinethione heterocyclic framework gave the corresponding N-boc protected esters 7d-f . Because bonds to the asymmetric carbon were not broken in any of the synthesized compounds, the stereochemistry of these reactions all proceeded with retention of ‘S’ configuration. All synthesized compounds were characterized by 1H NMR, 13C NMR, IR and MS spectral data.

Keywords

Oxazolidinones, oxazolidinethiones, synthesis

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