Oxepines and Azepines

Riley, Darren L.; Otterlo, Willem A. L. van

doi:10.1002/9783527634880.ch15

Cited by 8 publications

(6 citation statements)

References 132 publications

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“…The disadvantages of these methods are the lack of selectivity as well as of stereocontrol and hence other routes are needed. One interesting option is the pathway via oxepines [ 15 – 18 ] and the subsequent dihydroxylation or direct reduction of their C=C double bond to give the corresponding oxepane derivatives [ 19 – 20 ]. Alternatively, oxepanes were also synthesized by the ring enlargement of their six-membered homologues [ 21 – 22 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

Bouché¹,

Kandziora²,

Reißig³

2014

Beilstein J. Org. Chem.

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SummaryNew compounds with carbohydrate-similar structure (carbohydrate mimetics) are presented in this article. Starting from enantiopure nitrones and lithiated TMSE-allene we prepared three 1,2-oxazine derivatives which underwent a highly stereoselective Lewis acid-induced rearrangement to give bicyclic products in good yield. Subsequent reductive transformations delivered a library of new poly(hydroxy)aminooxepane derivatives. The crucial final palladium-catalyzed hydrogenolysis of the 1,2-oxazine moiety was optimized resulting in a reasonably efficient approach to a series of new seven-membered carbohydrate mimetics.

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Section: Introductionmentioning

confidence: 99%

Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

Bouché¹,

Kandziora²,

Reißig³

2014

Beilstein J. Org. Chem.

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“…Azepine- and oxepine-containing fused ring systems are found in some pharmacologically active compounds and in natural products, and their efficient synthesis is still highly challenging. Therefore, developing cycloaddition reactions of bisallenes with a third unsaturation being able to control the formation of a seven-membered ring is highly desirable.…”

mentioning

confidence: 99%

A Rh-Catalyzed Cycloisomerization/Diels–Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles

et al. 2019

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A novel methodology to transform bisallenes into a variety of polycyclic derivatives employing rhodium(I) catalysis has been developed. This transformation encompasses an intramolecular Rh-catalyzed cycloisomerization of bisallenes 1 to deliver a reactive cycloheptadiene, which concomitantly undergoes a regioselective [4+2] cycloaddition with alkenes. A complete mechanistic study of this transformation has been undertaken including DFT calculations. Overall, the methodology presented here constitutes a new and straightforward entry to polycyclic dihydroazepine and dihydrooxepine derivatives employing catalytic methods.

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“…Oxepine and hydrooxepine derivatives are core skeletons in numerous naturally occurring biologically active compounds. These compounds present interesting challenges as potential synthetic targets and can also be used as intermediates in heterocycle synthesis . Therefore, the synthesis of this class of O-heterocycles has received much attention.…”

mentioning

confidence: 99%

Iodine-Catalyzed Oxidative Coupling To Construct C–O Bonds for the Synthesis of 2,3-Dihydrooxepines

Geng

Zhao

et al. 2017

Org. Lett.

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The iodine-catalyzed catalytic formal [3 + 3 + 1] cycloaddition for the preparation of a seven-membered O-heterocyclic ring is presented, which is an achievement of methyl and carbonyl group reactivity of 3-methyl-5-pyrazolones to forge the C-O bond. This novel protocol provides a straightforward and efficient access to structurally diverse fused O-heterocycles through an iodine-catalyzed iodination/Kornblum oxidation/oxidative coupling/C-O bond formation cascade reaction. This approach demonstrates the unprecedented concurrent realization of the unique reactivity among the methyl, methylene, and carbonyl groups in 3-methyl-5-pyrazolones for the construction of 2,3-dihydrooxepine rings. Moreover, a broad substrate scope displays a graceful diversity-oriented synthetic approach.

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Oxepines and Azepines

Cited by 8 publications

References 132 publications

Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

A Rh-Catalyzed Cycloisomerization/Diels–Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles

Iodine-Catalyzed Oxidative Coupling To Construct C–O Bonds for the Synthesis of 2,3-Dihydrooxepines

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