Aerobic epoxidation and hydroxylation of a pyrrolo[2,1-b]quinazoline under ambient conditions

Ryan A. Hawkins; Chad E. Stephens

doi:10.1016/j.tetlet.2010.09.073

Aerobic epoxidation and hydroxylation of a pyrrolo[2,1-b]quinazoline under ambient conditions

Ryan A. Hawkins, Chad E. Stephens

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

4 Scopus citations

Abstract

A pyrrolo[2,1-b]quinazoline has been found to undergo both epoxidation and hydroxylation on the pyrrole nucleus upon simple exposure of an acetone solution to air or oxygen. The oxygenation reaction occurs most readily when the starting compound contains a t-butyl ester at the 3-position, compared to a cyano or phenylsulfonyl. The structure of the product has been confirmed by X-ray crystal analysis.

Original language	English (US)
Pages (from-to)	6129-6131
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	47
DOIs	https://doi.org/10.1016/j.tetlet.2010.09.073
State	Published - Nov 24 2010

Keywords

Aerobic epoxidation
Aerobic hydroxylation
Pyrrole oxygenation
Pyrrolo[2,1-b]quinazoline
Singlet oxygen

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2010.09.073

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title = "Aerobic epoxidation and hydroxylation of a pyrrolo[2,1-b]quinazoline under ambient conditions",

abstract = "A pyrrolo[2,1-b]quinazoline has been found to undergo both epoxidation and hydroxylation on the pyrrole nucleus upon simple exposure of an acetone solution to air or oxygen. The oxygenation reaction occurs most readily when the starting compound contains a t-butyl ester at the 3-position, compared to a cyano or phenylsulfonyl. The structure of the product has been confirmed by X-ray crystal analysis.",

keywords = "Aerobic epoxidation, Aerobic hydroxylation, Pyrrole oxygenation, Pyrrolo[2,1-b]quinazoline, Singlet oxygen",

author = "Hawkins, {Ryan A.} and Stephens, {Chad E.}",

note = "Funding Information: Funding for this research was provided by our Pamplin College of Arts and Sciences and the ASU Foundation . HRMS data was provided by the Mass Spectrometry Facility at Georgia State University. We thank Dr. Kenneth Hardcastle, Emory University X-ray Crystallography Center, for determination of the crystal structure and helpful comments. ",

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doi = "10.1016/j.tetlet.2010.09.073",

language = "English (US)",

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T1 - Aerobic epoxidation and hydroxylation of a pyrrolo[2,1-b]quinazoline under ambient conditions

AU - Hawkins, Ryan A.

AU - Stephens, Chad E.

N1 - Funding Information: Funding for this research was provided by our Pamplin College of Arts and Sciences and the ASU Foundation . HRMS data was provided by the Mass Spectrometry Facility at Georgia State University. We thank Dr. Kenneth Hardcastle, Emory University X-ray Crystallography Center, for determination of the crystal structure and helpful comments.

PY - 2010/11/24

Y1 - 2010/11/24

N2 - A pyrrolo[2,1-b]quinazoline has been found to undergo both epoxidation and hydroxylation on the pyrrole nucleus upon simple exposure of an acetone solution to air or oxygen. The oxygenation reaction occurs most readily when the starting compound contains a t-butyl ester at the 3-position, compared to a cyano or phenylsulfonyl. The structure of the product has been confirmed by X-ray crystal analysis.

AB - A pyrrolo[2,1-b]quinazoline has been found to undergo both epoxidation and hydroxylation on the pyrrole nucleus upon simple exposure of an acetone solution to air or oxygen. The oxygenation reaction occurs most readily when the starting compound contains a t-butyl ester at the 3-position, compared to a cyano or phenylsulfonyl. The structure of the product has been confirmed by X-ray crystal analysis.

KW - Aerobic epoxidation

KW - Aerobic hydroxylation

KW - Pyrrole oxygenation

KW - Pyrrolo[2,1-b]quinazoline

KW - Singlet oxygen

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DO - 10.1016/j.tetlet.2010.09.073

M3 - Article

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SN - 0040-4039

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EP - 6131

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 47

ER -

Aerobic epoxidation and hydroxylation of a pyrrolo[2,1-b]quinazoline under ambient conditions

Abstract

Keywords

ASJC Scopus subject areas

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