Transferring oxygen isotopes to 1,2,4-benzotriazine 1-oxides forming the corresponding 1,4-dioxides by using the HOF·CH 3CN complex

Julia Gatenyo; Kevin Johnson; Anuruddha Rajapakse; Kent S. Gates; Shlomo Rozen

doi:10.1016/j.tet.2012.08.017

Transferring oxygen isotopes to 1,2,4-benzotriazine 1-oxides forming the corresponding 1,4-dioxides by using the HOF·CH ₃CN complex

Julia Gatenyo, Kevin Johnson, Anuruddha Rajapakse, Kent S. Gates, Shlomo Rozen^*

^*Corresponding author for this work

School of Chemistry

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

Abstract

Heterocyclic benzotriazine N-oxides are an interesting class of experimental anticancer and antibacterial agents. Analogs with ¹⁸O incorporated into the N-oxide group may offer useful mechanistic tools. We describe the use of H ₂ ¹⁸OF·CH ₃CN in a fast, readily executed and high-yielding preparation of 1,2,4-benzotriazine 1,4-dioxides containing an ¹⁸O-label at the 4-oxide position.

Original language	English
Pages (from-to)	8942-8944
Number of pages	3
Journal	Tetrahedron
Volume	68
Issue number	43
DOIs	https://doi.org/10.1016/j.tet.2012.08.017
State	Published - 28 Oct 2012

Keywords

F /N
H O
HOF·CH CN
N-oxide
O isotope
Oxygen transfer
Tirapazamine

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10.1016/j.tet.2012.08.017

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title = "Transferring oxygen isotopes to 1,2,4-benzotriazine 1-oxides forming the corresponding 1,4-dioxides by using the HOF·CH 3CN complex",

abstract = "Heterocyclic benzotriazine N-oxides are an interesting class of experimental anticancer and antibacterial agents. Analogs with 18O incorporated into the N-oxide group may offer useful mechanistic tools. We describe the use of H 2 18OF·CH 3CN in a fast, readily executed and high-yielding preparation of 1,2,4-benzotriazine 1,4-dioxides containing an 18O-label at the 4-oxide position.",

keywords = "F /N, H O, HOF·CH CN, N-oxide, O isotope, Oxygen transfer, Tirapazamine",

author = "Julia Gatenyo and Kevin Johnson and Anuruddha Rajapakse and Gates, {Kent S.} and Shlomo Rozen",

year = "2012",

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doi = "10.1016/j.tet.2012.08.017",

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T1 - Transferring oxygen isotopes to 1,2,4-benzotriazine 1-oxides forming the corresponding 1,4-dioxides by using the HOF·CH 3CN complex

AU - Gatenyo, Julia

AU - Johnson, Kevin

AU - Rajapakse, Anuruddha

AU - Gates, Kent S.

AU - Rozen, Shlomo

PY - 2012/10/28

Y1 - 2012/10/28

N2 - Heterocyclic benzotriazine N-oxides are an interesting class of experimental anticancer and antibacterial agents. Analogs with 18O incorporated into the N-oxide group may offer useful mechanistic tools. We describe the use of H 2 18OF·CH 3CN in a fast, readily executed and high-yielding preparation of 1,2,4-benzotriazine 1,4-dioxides containing an 18O-label at the 4-oxide position.

AB - Heterocyclic benzotriazine N-oxides are an interesting class of experimental anticancer and antibacterial agents. Analogs with 18O incorporated into the N-oxide group may offer useful mechanistic tools. We describe the use of H 2 18OF·CH 3CN in a fast, readily executed and high-yielding preparation of 1,2,4-benzotriazine 1,4-dioxides containing an 18O-label at the 4-oxide position.

KW - F /N

KW - H O

KW - HOF·CH CN

KW - N-oxide

KW - O isotope

KW - Oxygen transfer

KW - Tirapazamine

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SN - 0040-4020

VL - 68

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JO - Tetrahedron

JF - Tetrahedron

IS - 43

ER -

Transferring oxygen isotopes to 1,2,4-benzotriazine 1-oxides forming the corresponding 1,4-dioxides by using the HOF·CH ₃CN complex

Abstract

Keywords

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