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Keywords = tosyloxy ketone

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8 pages, 1686 KB  
Communication
Straightforward Synthesis of 2(5H)-Furanones as Promising Cross-Coupling Partners: Direct Furanone Annulation Utilizing Ti-Mediated Aldol Addition
by Yuki Ban, Yuichiro Ashida, Hidefumi Nakatsuji and Yoo Tanabe
Molbank 2016, 2016(4), M908; https://doi.org/10.3390/M908 - 22 Sep 2016
Cited by 2 | Viewed by 5476
Abstract
Direct 2(5H)-furanone annulation produces promising cross-coupling partners incorporating m- or p-bromo- and p-tosyloxyphenyl groups into the 5-position of a notable 2(5H)-furanone pharmacore. The present one-pot annulation method involves two distinctive reactions: (i) a powerful and crossed [...] Read more.
Direct 2(5H)-furanone annulation produces promising cross-coupling partners incorporating m- or p-bromo- and p-tosyloxyphenyl groups into the 5-position of a notable 2(5H)-furanone pharmacore. The present one-pot annulation method involves two distinctive reactions: (i) a powerful and crossed Ti-direct aldol addition and (ii) an acid-induced characteristic cyclo-condensation, leading to 2(5H)-furanones. Suzuki-Miyaura cross-coupling of 5-(4-bromophenyl)-furan-2(5H)-ones, 5-(4-tosyloxyphenyl)-3,4-dimethylfuran-2(5H)-ones and a furan derivative successfully afforded the corresponding products with the 2(5H)-furanone skeleton. Full article
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5 pages, 62 KB  
Communication
[Hydroxy(tosyloxy)iodo]benzene Mediated α-Azidation of Ketones
by Om Prakash, Kamaljeet Pannu, Richa Prakash and Anita Batra
Molecules 2006, 11(7), 523-527; https://doi.org/10.3390/11070523 - 14 Jul 2006
Cited by 29 | Viewed by 9288
Abstract
Reaction of various ketones with [hydroxy(tosyloxy)iodo]benzene (HTIB) followed by treatment of the α-tosyloxy ketones thus generated in situ with NaN3 offers a one-pot procedure for the synthesis of α-azido ketones. The HTIB used in this conversion may also be generated in situ by [...] Read more.
Reaction of various ketones with [hydroxy(tosyloxy)iodo]benzene (HTIB) followed by treatment of the α-tosyloxy ketones thus generated in situ with NaN3 offers a one-pot procedure for the synthesis of α-azido ketones. The HTIB used in this conversion may also be generated in situ by using iodosobenzene in combination with p-toluene- sulphonic acid. Full article
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14 pages, 104 KB  
Review
Hypervalent Iodine–Mediated Ring Contraction Reactions
by Luiz F. Silva
Molecules 2006, 11(6), 421-434; https://doi.org/10.3390/11060421 - 20 Jun 2006
Cited by 75 | Viewed by 14595
Abstract
Hypervalent iodine reagents constitute a powerful tool in modern synthetic organic chemistry, promoting several important reactions. One such reaction is the ring contraction of cycloalkenes and cycloalkanones promoted by iodine(III) compounds, such as iodobenzene diacetate, iodosylbenzene, iodotoluene difluoride, and [hydroxy(tosyloxy)- iodo]benzene (Koser ́s [...] Read more.
Hypervalent iodine reagents constitute a powerful tool in modern synthetic organic chemistry, promoting several important reactions. One such reaction is the ring contraction of cycloalkenes and cycloalkanones promoted by iodine(III) compounds, such as iodobenzene diacetate, iodosylbenzene, iodotoluene difluoride, and [hydroxy(tosyloxy)- iodo]benzene (Koser ́s reagent). This review covers all the literature related to the ring contraction of cyclic ketones and olefins promoted by iodine(III) species. Full article
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