The Synthesis of 5-Substituted 1,2,3-Triazines with Ketene Silyl Acetals and Ceric Ammonium Nitrate

Takashi Itoh; Yuji Matsuya; Hiroshi Hasegawa; Kazuhiro Nagata; Mamiko Okada; Akio Ohsawa

doi:10.1248/cpb.43.881

The Synthesis of 5-Substituted 1,2,3-Triazines with Ketene Silyl Acetals and Ceric Ammonium Nitrate

Takashi Itoh, Yuji Matsuya, Hiroshi Hasegawa, Kazuhiro Nagata, Mamiko Okada, Akio Ohsawa^*

^*Corresponding author for this work

Synthetic and Medicinal Chemistry

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

7 Scopus citations

Abstract

Monocyclic 1,2,3-triazines were reacted with ketene silyl acetal or silyl enol ether in the presence of 1-chloroethyl chloroformate to give 5-substituted 2-(l-chloroethoxycarbonyl)-2,5-dihydrotriazines. These dihydro-adducts were readily oxidized and hydrolyzed with ceric ammonium nitrate in CH3CN/H2O to afford 5-substituted triazines.

Original language	English
Pages (from-to)	881-883
Number of pages	3
Journal	Chemical and Pharmaceutical Bulletin
Volume	43
Issue number	5
DOIs	https://doi.org/10.1248/cpb.43.881
State	Published - 1995

Keywords

1,2,3-triazine
1-chloroethyl chloroformate
ceric ammonium nitrate
ketene silyl acetal

ASJC Scopus subject areas

General Chemistry
Drug Discovery

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title = "The Synthesis of 5-Substituted 1,2,3-Triazines with Ketene Silyl Acetals and Ceric Ammonium Nitrate",

abstract = "Monocyclic 1,2,3-triazines were reacted with ketene silyl acetal or silyl enol ether in the presence of 1-chloroethyl chloroformate to give 5-substituted 2-(l-chloroethoxycarbonyl)-2,5-dihydrotriazines. These dihydro-adducts were readily oxidized and hydrolyzed with ceric ammonium nitrate in CH3CN/H2O to afford 5-substituted triazines.",

keywords = "1,2,3-triazine, 1-chloroethyl chloroformate, ceric ammonium nitrate, ketene silyl acetal",

author = "Takashi Itoh and Yuji Matsuya and Hiroshi Hasegawa and Kazuhiro Nagata and Mamiko Okada and Akio Ohsawa",

year = "1995",

doi = "10.1248/cpb.43.881",

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T1 - The Synthesis of 5-Substituted 1,2,3-Triazines with Ketene Silyl Acetals and Ceric Ammonium Nitrate

AU - Itoh, Takashi

AU - Matsuya, Yuji

AU - Hasegawa, Hiroshi

AU - Nagata, Kazuhiro

AU - Okada, Mamiko

AU - Ohsawa, Akio

PY - 1995

Y1 - 1995

N2 - Monocyclic 1,2,3-triazines were reacted with ketene silyl acetal or silyl enol ether in the presence of 1-chloroethyl chloroformate to give 5-substituted 2-(l-chloroethoxycarbonyl)-2,5-dihydrotriazines. These dihydro-adducts were readily oxidized and hydrolyzed with ceric ammonium nitrate in CH3CN/H2O to afford 5-substituted triazines.

AB - Monocyclic 1,2,3-triazines were reacted with ketene silyl acetal or silyl enol ether in the presence of 1-chloroethyl chloroformate to give 5-substituted 2-(l-chloroethoxycarbonyl)-2,5-dihydrotriazines. These dihydro-adducts were readily oxidized and hydrolyzed with ceric ammonium nitrate in CH3CN/H2O to afford 5-substituted triazines.

KW - 1,2,3-triazine

KW - 1-chloroethyl chloroformate

KW - ceric ammonium nitrate

KW - ketene silyl acetal

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U2 - 10.1248/cpb.43.881

DO - 10.1248/cpb.43.881

M3 - 学術論文

AN - SCOPUS:0029021789

SN - 0009-2363

VL - 43

SP - 881

EP - 883

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 5

ER -

The Synthesis of 5-Substituted 1,2,3-Triazines with Ketene Silyl Acetals and Ceric Ammonium Nitrate

Abstract

Keywords

ASJC Scopus subject areas

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