Ring-expansion reaction of oximes with aluminum reductants

Hidetsura Cho; Yusuke Iwama; Nakako Mitsuhashi; Kenji Sugimoto; Kentaro Okano; Hidetoshi Tokuyama

doi:10.3390/molecules17067348

Ring-expansion reaction of oximes with aluminum reductants

Hidetsura Cho, Yusuke Iwama, Nakako Mitsuhashi, Kenji Sugimoto, Kentaro Okano, Hidetoshi Tokuyama

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl ₂, AlH ₃ (alane), LiAlH ₄, LiAlH(OtBu) ₃, and (MeOCH ₂CH ₂O) ₂AlH ₂Na (Red-Al) were examined. Among reductants, AlHCl ₂ (LiAlH ₄:AlCl ₃ = 1:3) in cyclopentyl methyl ether (CPME) has been found to be a suitable reagent for the reaction, and the rearranged cyclic secondary amines were obtained in good to excellent yields.

Original language	English
Pages (from-to)	7348-7355
Number of pages	8
Journal	Molecules
Volume	17
Issue number	6
DOIs	https://doi.org/10.3390/molecules17067348
Publication status	Published - 2012 Jun

Keywords

Aluminum reductant
Cyclopentyl methyl ether (CPME)
Dichloroaluminum hydride (AlHCl )
Rearrangement of oxime
Ring-expansion of oxime

ASJC Scopus subject areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Ring-expansion reaction of oximes with aluminum reductants",

abstract = "The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl 2, AlH 3 (alane), LiAlH 4, LiAlH(OtBu) 3, and (MeOCH 2CH 2O) 2AlH 2Na (Red-Al) were examined. Among reductants, AlHCl 2 (LiAlH 4:AlCl 3 = 1:3) in cyclopentyl methyl ether (CPME) has been found to be a suitable reagent for the reaction, and the rearranged cyclic secondary amines were obtained in good to excellent yields.",

keywords = "Aluminum reductant, Cyclopentyl methyl ether (CPME), Dichloroaluminum hydride (AlHCl ), Rearrangement of oxime, Ring-expansion of oxime",

author = "Hidetsura Cho and Yusuke Iwama and Nakako Mitsuhashi and Kenji Sugimoto and Kentaro Okano and Hidetoshi Tokuyama",

year = "2012",

month = jun,

doi = "10.3390/molecules17067348",

language = "English",

volume = "17",

pages = "7348--7355",

journal = "Molecules",

issn = "1420-3049",

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T1 - Ring-expansion reaction of oximes with aluminum reductants

AU - Cho, Hidetsura

AU - Iwama, Yusuke

AU - Mitsuhashi, Nakako

AU - Sugimoto, Kenji

AU - Okano, Kentaro

AU - Tokuyama, Hidetoshi

PY - 2012/6

Y1 - 2012/6

N2 - The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl 2, AlH 3 (alane), LiAlH 4, LiAlH(OtBu) 3, and (MeOCH 2CH 2O) 2AlH 2Na (Red-Al) were examined. Among reductants, AlHCl 2 (LiAlH 4:AlCl 3 = 1:3) in cyclopentyl methyl ether (CPME) has been found to be a suitable reagent for the reaction, and the rearranged cyclic secondary amines were obtained in good to excellent yields.

AB - The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl 2, AlH 3 (alane), LiAlH 4, LiAlH(OtBu) 3, and (MeOCH 2CH 2O) 2AlH 2Na (Red-Al) were examined. Among reductants, AlHCl 2 (LiAlH 4:AlCl 3 = 1:3) in cyclopentyl methyl ether (CPME) has been found to be a suitable reagent for the reaction, and the rearranged cyclic secondary amines were obtained in good to excellent yields.

KW - Aluminum reductant

KW - Cyclopentyl methyl ether (CPME)

KW - Dichloroaluminum hydride (AlHCl )

KW - Rearrangement of oxime

KW - Ring-expansion of oxime

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