synthesis of new 2-halo-2-(1h-tetrazol-5-yl)-2h-azirines via a non-classical wittig reaction
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ID: 198730
2015
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Abstract
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.
| Reference Key |
cardoso2015moleculessynthesis
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|---|---|
| Authors | ;Ana L. Cardoso;Carmo Sousa;Marta S. C. Henriques;José A. Paixão;Teresa M. V. D. Pinho e Melo |
| Journal | Journal of ethnopharmacology |
| Year | 2015 |
| DOI |
10.3390/molecules201219848
|
| URL | |
| Keywords | Keywords not found |
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