Addition des composés nitrosés sur un système conjugué

Wichterle, O.

doi:10.1135/cccc19470292

Cited by 64 publications

(38 citation statements)

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“…[2][3][4][5] Products of HDA reactions, N-aryldihydro [1,2]oxazines, are amenable to further transformations in a manner analogous to acylnitroso HDA adducts. In the previous paper, 6 we described the results of HDA reactions of dienes with polymer-supported acylnitroso dienophiles.…”

Section: Introductionmentioning

confidence: 99%

Solid-Supported Nitroso Hetero Diels–Alder Reactions. 2. Arylnitroso Dienophiles: Scope and Limitations

Krchňák

Moellmann²,

Dahse³

et al. 2008

J. Comb. Chem.

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Immobilized arylnitroso dienophiles were prepared and used in hetero Diels-Alder (HDA) reactions with a variety of dienes. Polymer-supported arylnitroso species were prepared on several linkers cleavable by different cleavage reagents and used for (i) optimization of reaction conditions for HDA reactions, (ii) evaluation of the reaction outcome with various dienes, (iii) comparison of relative reactivities of dienes, and (iv) assessment of the stability of HDA adducts toward cleavage conditions typically used in solid-phase preparation (TFA). The outcome of the HDA reactions has been evaluated for a set of 19 dienes, and the relative reactivities of dienes that yielded the expected HDA adducts were compared. Cleaved products were submitted to biological assays, and the results are reported.

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Section: Introductionmentioning

confidence: 99%

Solid-Supported Nitroso Hetero Diels–Alder Reactions. 2. Arylnitroso Dienophiles: Scope and Limitations

Krchňák

Moellmann²,

Dahse³

et al. 2008

J. Comb. Chem.

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“…The first nitroso hetero-Diels–Alder reactions using alkyl- or arylnitroso dienophiles were reported by Wichterle [11] and Arbuzov [12–13] in 1947 and 1948, respectively. Among the early reported reactions using an acylnitroso compound as the dienophile, an interesting study by Kirby and Sweeny in 1973 [14] reported that the acylnitroso dienophile 5 was generated in the presence of thebaine ( 4 ) to selectively give the 1,2-oxazine 6 (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

Stereo- and regioselectivity of the hetero-Diels–Alder reaction of nitroso derivatives with conjugated dienes

Brulíková

Harrison

Miller

et al. 2016

Beilstein J. Org. Chem.

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SummaryThe hetero-Diels–Alder reaction between a nitroso dienophile and a conjugated diene to give the 3,6-dihydro-2H-1,2-oxazine scaffold is useful for the synthesis of many biologically interesting molecules due to the diverse opportunities created by subsequent transformations of the resulting 1,2-oxazine ring. This review discusses the rationale for the observed regio- and stereoselectivity and the methods developed in recent years used to control and improve the stereo- and regioselectivity for the synthesis of 1,2-oxazine scaffolds.

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“…Since 1947 and the pioneering work of Wichterle, 1 this reaction has been widely studied and numerous nitroso and diene partners have been used to enlarge its scope and efficiency. A large range of nitroso reagents, including acylnitroso, nitrosoarene and chloronitroso etc., have been used, as well as substituted acyclic, cyclic and heterocyclic dienes to provide 3,6-dihydro-1,2-oxazine scaffolds.…”

Section: Introductionmentioning

confidence: 99%

Regioisomeric and Substituent Effects upon the Outcome of the Reaction of 1-Borodienes with Nitrosoarene Compounds

2015

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(2015) 'Regioisomeric and substituent eects upon the outcome of the reaction of 1-borodienes with nitrosoarene compounds.', Journal of organic chemistry., 80 (13). pp. 6574-6583. Further information on publisher's website:http://dx.doi.org/10.1021/acs.joc.5b00593Publisher's copyright statement:This document is the Accepted Manuscript version of a Published Work that appeared in nal form in The Journal of Organic Chemistry, copyright c 2015 American Chemical Society after peer review and technical editing by the publisher. To access the nal edited and published work see http://dx.doi.org/10.1021/acs.joc.5b00593. Additional information:Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. with high regioselectivity in most of cases, in moderate to good yield. 1 H and 11 B NMR studies on two boro-oxazine regioisomers showed that selective deprotection can be performed.Formation of either the pyrrole or furan derivative is pH and regioisomer-structure dependent.The results obtained, together with previous B3LYP calculations, support mechanistic proposals which suggest that pyrrole, or furan formation, proceeds via oxazine formation, followed by a boryl rearrangement and an intramolecular addition-elimination sequence.

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Addition des composés nitrosés sur un système conjugué

Cited by 64 publications

References 0 publications

Solid-Supported Nitroso Hetero Diels–Alder Reactions. 2. Arylnitroso Dienophiles: Scope and Limitations

Solid-Supported Nitroso Hetero Diels–Alder Reactions. 2. Arylnitroso Dienophiles: Scope and Limitations

Stereo- and regioselectivity of the hetero-Diels–Alder reaction of nitroso derivatives with conjugated dienes

Regioisomeric and Substituent Effects upon the Outcome of the Reaction of 1-Borodienes with Nitrosoarene Compounds

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