Regiospecific synthesis of unsubstituted basic skeletons of heterocycles containing nitrogen neighboring an aromatic ring by the reductive ring expansion reaction using diisobutylaluminum hydride

Hidetsura Cho; Yusuke Iwama; Kenji Sugimoto; Eunsang Kwon; Hidetoshi Tokuyama

doi:10.3987/COM-08-11629

Regiospecific synthesis of unsubstituted basic skeletons of heterocycles containing nitrogen neighboring an aromatic ring by the reductive ring expansion reaction using diisobutylaluminum hydride

Hidetsura Cho, Yusuke Iwama, Kenji Sugimoto, Eunsang Kwon, Hidetoshi Tokuyama

Tohoku University

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

22 Citations (Scopus)

Abstract

A systematic investigation of reductive ring expansion reaction of oximes with diisobutylaluminum hydride (DIBAH) was performed. The reaction regiospecifically provided a variety of unsubstituted bicyclic heterocycles 3a-3g or tricyclic heterocycles 3h, 3j-3l that contained nitrogen attached to an aromatic ring.

Original language	English
Pages (from-to)	1183-1190
Number of pages	8
Journal	Heterocycles
Volume	78
Issue number	5
DOIs	https://doi.org/10.3987/COM-08-11629
Publication status	Published - 2009 May 1

Keywords

Diisobutylaluminum Hydride (DIBAH)
Rearrangement
Regiospecitic Synthesis
Ring Expansion
Unsubstituted Basic Skeleton

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10.3987/COM-08-11629

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abstract = "A systematic investigation of reductive ring expansion reaction of oximes with diisobutylaluminum hydride (DIBAH) was performed. The reaction regiospecifically provided a variety of unsubstituted bicyclic heterocycles 3a-3g or tricyclic heterocycles 3h, 3j-3l that contained nitrogen attached to an aromatic ring.",

keywords = "Diisobutylaluminum Hydride (DIBAH), Rearrangement, Regiospecitic Synthesis, Ring Expansion, Unsubstituted Basic Skeleton",

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Regiospecific synthesis of unsubstituted basic skeletons of heterocycles containing nitrogen neighboring an aromatic ring by the reductive ring expansion reaction using diisobutylaluminum hydride. / Cho, Hidetsura; Iwama, Yusuke; Sugimoto, Kenji et al.
In: Heterocycles, Vol. 78, No. 5, 01.05.2009, p. 1183-1190.

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

TY - JOUR

T1 - Regiospecific synthesis of unsubstituted basic skeletons of heterocycles containing nitrogen neighboring an aromatic ring by the reductive ring expansion reaction using diisobutylaluminum hydride

AU - Cho, Hidetsura

AU - Iwama, Yusuke

AU - Sugimoto, Kenji

AU - Kwon, Eunsang

AU - Tokuyama, Hidetoshi

PY - 2009/5/1

Y1 - 2009/5/1

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AB - A systematic investigation of reductive ring expansion reaction of oximes with diisobutylaluminum hydride (DIBAH) was performed. The reaction regiospecifically provided a variety of unsubstituted bicyclic heterocycles 3a-3g or tricyclic heterocycles 3h, 3j-3l that contained nitrogen attached to an aromatic ring.

KW - Diisobutylaluminum Hydride (DIBAH)

KW - Rearrangement

KW - Regiospecitic Synthesis

KW - Ring Expansion

KW - Unsubstituted Basic Skeleton

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Regiospecific synthesis of unsubstituted basic skeletons of heterocycles containing nitrogen neighboring an aromatic ring by the reductive ring expansion reaction using diisobutylaluminum hydride

Abstract

Keywords

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