Preparation and properties of novel hetero-halogen complexes

Nishidai, Yuji; Kawabata, Toshiki; Yubata, Kotaro; Ota, Fumiya; Takamiya, Hiroki; Fujiwara, Hideki; Matsubara, Hiroshi

doi:10.1016/j.tet.2022.132854

Tetrahedron

2022

DOI: 10.1016/j.tet.2022.132854

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Preparation and properties of novel hetero-halogen complexes

Yuji Nishidai¹,

Toshiki Kawabata²,

Kotaro Yubata³

et al.

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2023

2024

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Cited by 2 publications

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“…27 Based on generally accepted mechanistic concepts in this field of organic chemistry, it can be assumed that in these halogenation reactions and the subsequent formation of an aryl-fused eight-membered ring several intermediate stages are possible for the conversion of glycine I. It is quite possible that at each of these stages the formation of its final reaction product is expected, also including the direction where the mechanism of classical n-exo-halocyclization (n = 5,6,7,…) is realized, [28][29][30][31] which would lead to a spirocyclic molecule. The last direction, if there were no experimental results, in this case looks like a more realistic outcome of this transformation.…”

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confidence: 99%

Halolactonization of N-Acyl-N-(2-cyclohex-1-en-1-yl-6-methylphenyl)glycines: Towards Production of 4,1-Benzoxazoheterocycles

Гатауллин¹

2023

Synthesis

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A significant influence of the nature of the acyl substituent at the nitrogen atom on the direction of the reaction in the interaction of N-acyl-N-(2-cyclohex-1-en-1-yl-6-methylphenyl)glycines with bromine was found. In the case of the N-benzoyl derivative, along with benzoxazocinone, which is formed through the stages of pseudoallyl halogenation and subsequent lactonization due to the replacement of the bromine atom by the oxygen atom of the carboxyl group, a mixture of axially chiral isomers of spiro-fused 2′-bromocyclohexane-benzoxazepin-3-ones was also obtained. The aR*,R*,R*-isomer of benzoxazepinone, which initially is four times predominant in the reaction mixture, upon dissolution in deuterochloroform, slowly transforms into aS*-conformer until a ratio of 2:1 is established. In the case of the N-acetyl analogue of this glycine, the only heterocycle is the product of 7-exo-halogenlactonization, the benzoxazepinone spiro-fused with 2′-bromocyclohexane and an undetermined configuration of the axial chirality.

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mentioning

confidence: 99%

Halolactonization of N-Acyl-N-(2-cyclohex-1-en-1-yl-6-methylphenyl)glycines: Towards Production of 4,1-Benzoxazoheterocycles

Гатауллин¹

2023

Synthesis

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Lactonization of N-Acyl-N-(2-cyclopent-1-en-1-yl-6-methylphenyl)glycines upon Raction with Halogens

Gataullin,

Meshcheryakova,

Khalilov

2024

Žurnal obŝej himii

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A study was carried out to identify the influence of the size of the cycloalkenyl ring and the nature of the substituent at the nitrogen atom on the structure and stability of the halogen cyclization products N-acyl-N-(2-cyclopent-1-en-1-yl-6-methylphenyl)glycines, which were synthesized from N-acyl-2-(1-cyclopenten-1-yl)-6-methylanilines and methyl bromoacetate followed by alkaline hydrolysis of the resulting methyl glycinates. It was shown that in the reaction of N-benzoyl and N-(4-nitrobenzoyl) derivatives with molecular bromine, 2′-bromo-9-methyl-N-aroyl-1,2-dihydro-3H-spiro[4,1-benzoxazepine-5,1′-cyclopentan]-3-ones and 8-methyl-N-aroyl-3,3a,6,7- tetrahydrobenzo[e]cyclopenta[g][1,4]oxazocin-5(2H)-ones is formed, the ratio of which in the case of the N-benzoyl derivative is ≈1:4, in the case of the N-nitrobenzoyl analogue reaches ≈1:1. Spiro-fused benzoxazepinones, unlike eight-membered heterocycles, are unstable. Samples of these compounds isolated by chromatography decompose with strong darkening within a few hours. In the case of the N-acetyl homologue, the resulting halogenlactonization products cannot be isolated due to their rapid decomposition. The aS*,R*-configuration of the substituents along the N⁷–C⁷a axis and at C³a center of chirality of N-aroylbenzoxazocinones was established by X-ray diffraction studies.

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Preparation and properties of novel hetero-halogen complexes

Cited by 2 publications

References 60 publications

Halolactonization of N-Acyl-N-(2-cyclohex-1-en-1-yl-6-methylphenyl)glycines: Towards Production of 4,1-Benzoxazoheterocycles

Halolactonization of N-Acyl-N-(2-cyclohex-1-en-1-yl-6-methylphenyl)glycines: Towards Production of 4,1-Benzoxazoheterocycles

Lactonization of N-Acyl-N-(2-cyclopent-1-en-1-yl-6-methylphenyl)glycines upon Raction with Halogens

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