(s)-(-)-limonene derivatives containing (1h-1,2,3-triazol-4-yl)methyl 4-bromobenzoate(s)-(-)衍生品含有柠檬烯(1 h - 2 3-triazol-4-yl)甲基4-bromobenzoate.pdfVIP

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(s)-(-)-limonene derivatives containing (1h-1,2,3-triazol-4-yl)methyl 4-bromobenzoate(s)-(-)衍生品含有柠檬烯(1 h - 2 3-triazol-4-yl)甲基4-bromobenzoate.pdf

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(s)-(-)-limonene derivatives containing (1h-1,2,3-triazol-4-yl)methyl 4-bromobenzoate(s)-(-)衍生品含有柠檬烯(1 h - 2 3-triazol-4-yl)甲基4-bromobenzoate

Molbank 2011, M721; doi:10.3390/M721 OPEN ACCESS molbank ISSN 1422-8599 /journal/molbank Short Note (S)-(-)-Limonene Derivatives Containing (1H-1,2,3-Triazol-4- yl)methyl 4-Bromobenzoate Guillermo Valdomir and Danilo Davyt * Cátedra de Química Farmacéutica, Departamento de Química Orgánica, Facultad de Química, Universidad de la República (UdelaR), CC 1157, Av. General Flores 2124, Montevideo, Uruguay * Author to whom correspondence should be addressed; E-Mail: ddavyt@.uy. Received: 9 February 2011 / Accepted: 18 March 2011 / Published: 23 March 2011 Abstract: The synthesis of (S)-(-)-limonene derivatives containing (1H-1,2,3-triazol-4- yl)methyl 4-bromobenzoate were obtained by epoxidation, azidolysis and Huisgen’s 1,3- dipolar cycloaddition. Two products were isolated and characterized by FT-IR, 1H NMR, 13C NMR, ESI-MS and optical rotation. Keywords: Huisgen reaction; click chemistry; limonene 1. Introduction The use of natural products as starting material is a very attractive concept in order to use renewable, inexpensive and enantiomerically pure compounds. In this work, were synthesized two derivatives of (S)-(-)-limonene. These novel structures were created following the rules of click chemistry [1] and these reactions can be easily made over similar natural substrates. 2. Results and Discussions Complete epoxidation of (S)-(-)-limonene was performed with m-chloroperbenzoic acid, followed by azidolysis of epoxides with sodium azide and ammonium chloride in refluxing met