Synthesis of New 2-Halo-2-(1H-tetrazol-5-yl)-2H-azirines via a Non-Classical Wittig Reaction

Molecules

Ana L. Cardoso²  Carmo Sousa²  Marta S. C. Henriques¹  José A. Paixão¹  Teresa M. V. D. Pinho e Melo² 

[1] CFisUC and Department of Physics, University of Coimbra, Coimbra P-3004-516, Portugal;Centro de Química de Coimbra and Department of Chemistry, University of Coimbra, Coimbra 3004-535, Portugal;

关键词: 2-halo-2H-azirines;    vinyl tetrazoles;    tetrasubstituted alkenes;    phosphorus ylides;   

DOI  :  10.3390/molecules201219848

来源: mdpi

【 摘 要 】

The synthesis and reactivity of tetrazol-5-yl-phosphorus ylides towards N-halosuccinimide/TMSN₃ reagent systems was explored, opening the way to new haloazidoalkenes bearing a tetrazol-5-yl substituent. These compounds were obtained as single isomers, except in one case. X-ray crystal structures were determined for three derivatives, establishing that the non-classical Wittig reaction leads to the selective synthesis of haloazidoalkenes with (Z)-configuration. The thermolysis of the haloazidoalkenes afforded new 2-halo-2-(tetrazol-5-yl)-2H-azirines in high yields. Thus, the reported synthetic methodologies gave access to important building blocks in organic synthesis, vinyl tetrazoles and 2-halo-2-(tetrazol-5-yl)-2H-azirine derivatives.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.