Hypervalent Iodine-Catalyzed Synthesis of 1,2,4-Oxadiazoles from Aldoximes and Nitriles
| Parent link: | Asian Journal of Organic Chemistry Vol. 5, iss. 9.— 2016.— [P. 1128–1133] |
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| Corporate Author: | |
| Other Authors: | , , , , , , , |
| Summary: | Title screen A convenient procedure for oxidative cycloaddition of aldoximes with nitriles using stoichiometric or catalytic amounts of hypervalent iodine(III) reagent IBA-OTf (2-iodosylbenzoic acid triflate) has been developed. This efficient procedure works well for the preparation of various 1,2,4-oxadiazoles in generally high yields under mild reaction conditions. The actual oxidant in this reaction, IBA-OTf, is prepared from 2-iodosylbenzoic acid (IBA) and trifluoromethanesulfonic acid (TfOH) or it can be generated in situ from 2-iodobenzoic acid and m-chloroperoxybenzoic acid (m-CPBA) in the presence of TfOH. The nature of hydroxy(aryl)iodonium species, generated in situ from 2-iodobenzoic acid, m-CPBA, and TfOH under catalytic reaction conditions, has been confirmed by 1H?NMR spectroscopy, ESI-mass spectrometry, and by X-ray diffraction. Режим доступа: по договору с организацией-держателем ресурса |
| Language: | English |
| Published: |
2016
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| Subjects: | |
| Online Access: | http://dx.doi.org/10.1002/ajoc.201600247 |
| Format: | Electronic Book Chapter |
| KOHA link: | https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=651213 |
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| 200 | 1 | |a Hypervalent Iodine-Catalyzed Synthesis of 1,2,4-Oxadiazoles from Aldoximes and Nitriles |f A. Yoshimura [et al.] | |
| 203 | |a Text |c electronic | ||
| 300 | |a Title screen | ||
| 320 | |a [References: p. 1132-1133 (8 tit.)] | ||
| 330 | |a A convenient procedure for oxidative cycloaddition of aldoximes with nitriles using stoichiometric or catalytic amounts of hypervalent iodine(III) reagent IBA-OTf (2-iodosylbenzoic acid triflate) has been developed. This efficient procedure works well for the preparation of various 1,2,4-oxadiazoles in generally high yields under mild reaction conditions. The actual oxidant in this reaction, IBA-OTf, is prepared from 2-iodosylbenzoic acid (IBA) and trifluoromethanesulfonic acid (TfOH) or it can be generated in situ from 2-iodobenzoic acid and m-chloroperoxybenzoic acid (m-CPBA) in the presence of TfOH. The nature of hydroxy(aryl)iodonium species, generated in situ from 2-iodobenzoic acid, m-CPBA, and TfOH under catalytic reaction conditions, has been confirmed by 1H?NMR spectroscopy, ESI-mass spectrometry, and by X-ray diffraction. | ||
| 333 | |a Режим доступа: по договору с организацией-держателем ресурса | ||
| 461 | |t Asian Journal of Organic Chemistry | ||
| 463 | |t Vol. 5, iss. 9 |v [P. 1128–1133] |d 2016 | ||
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| 701 | 0 | |a Nguyen Khiem | |
| 701 | 1 | |a Klasen |b S. C. |g Scott | |
| 701 | 1 | |a Postnikov |b P. S. |c organic chemist |c Associate Professor of Tomsk Polytechnic University, Candidate of chemical sciences |f 1984- |g Pavel Sergeevich |3 (RuTPU)RU\TPU\pers\31287 |9 15465 | |
| 701 | 1 | |a Yusubov |b M. S. |c chemist |c Professor of Tomsk Polytechnic University, Doctor of chemical sciences |f 1961- |g Mekhman Suleiman-Ogly (Suleimanovich) |3 (RuTPU)RU\TPU\pers\31833 |9 15928 | |
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| 701 | 1 | |a Nemykin |b V. N. |g Viktor Nikolaevich | |
| 701 | 1 | |a Zhdankin |b V. V. |g Viktor | |
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