(N-Isocyanimino)triphenylphosphorane-Mediated,One-Pot,Efficient Synthesis of Sterically Congested 1,1,1-Trifluoro-2-(5-aryl-1,3,4-oxadiazol-2-yl)-2-propanol Derivatives via Intramolecular Aza-Wittig Reaction |
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| Authors: | Ali Ramazani Nahid Shajari Amir Tofangchi Mahyari Mehdi Khoobi Yavar Ahmadi Ali Souldozi |
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| Institution: | 1. Chemistry Department , Zanjan University , Zanjan, Iran;2. Member of Young Researchers Club , Islamic Azad University , Zanjan Branch, Zanjan, Iran;3. Chemistry Department , Islamic Azad University–Urmia Branch , Urmia, Iran |
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| Abstract: | Reactions of (N-isocyanimino)triphenylphosphorane with 1,1,1-trifluoroacetone in the presence of aromatic (or heteroaromatic) carboxylic acids (3-methylbenzoic acid, 1-naphthalenecarboxylic acid, 2-naphthalenecarboxylic acid, 2-furancarboxylic acid, and 2-thiophenecarboxylic acid) proceed smoothly at room temperature and in neutral conditions to afford sterically congested 1,1,1-trifluoro-2-(5-aryl-1,3,4-oxadiazol-2-yl)-2-propanol derivatives in high yields. The reaction proceeds smoothly and cleanly under mild conditions, and no side reactions were observed. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. |
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| Keywords: | Aromatic carboxylic acid aza-Wittig reaction heteroaromatic carboxylic acid (N-isocyanimino)triphenylphosphorane 1 3 4-oxadiazole 1 1 1-trifluoroacetone |
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