Palladium-catalyzed denitrogenation reaction of 1,2,3-benzotriazin-4(3 H)-ones incorporating isocyanides

Tomoya Miura; Yui Nishida; Masao Morimoto; Motoshi Yamauchi; Masahiro Murakami

doi:10.1021/ol103143a

Palladium-catalyzed denitrogenation reaction of 1,2,3-benzotriazin-4(3 H)-ones incorporating isocyanides

Tomoya Miura, Yui Nishida, Masao Morimoto, Motoshi Yamauchi, Masahiro Murakami

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

78 Citations (Scopus)

Abstract

1,2,3-Benzotriazin-4(3H)-ones and 1,2,3,4-benzothiatriazine 1,1(2H)-dioxide reacted with isocyanides in the presence of a palladium catalyst to give 3-(imino)isoindolin-1-ones and 3-(imino)thiaisoindoline 1,1-dioxides, respectively, in high yield. An intermediate azapalladacycle was generated through denitrogenation of the triazine moiety, and an isocyanide was incorporated therein.

Original language	English
Pages (from-to)	1429-1431
Number of pages	3
Journal	Organic Letters
Volume	13
Issue number	6
DOIs	https://doi.org/10.1021/ol103143a
Publication status	Published - Mar 18 2011
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Palladium-catalyzed denitrogenation reaction of 1,2,3-benzotriazin-4(3 H)-ones incorporating isocyanides",

abstract = "1,2,3-Benzotriazin-4(3H)-ones and 1,2,3,4-benzothiatriazine 1,1(2H)-dioxide reacted with isocyanides in the presence of a palladium catalyst to give 3-(imino)isoindolin-1-ones and 3-(imino)thiaisoindoline 1,1-dioxides, respectively, in high yield. An intermediate azapalladacycle was generated through denitrogenation of the triazine moiety, and an isocyanide was incorporated therein.",

author = "Tomoya Miura and Yui Nishida and Masao Morimoto and Motoshi Yamauchi and Masahiro Murakami",

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T1 - Palladium-catalyzed denitrogenation reaction of 1,2,3-benzotriazin-4(3 H)-ones incorporating isocyanides

AU - Miura, Tomoya

AU - Nishida, Yui

AU - Morimoto, Masao

AU - Yamauchi, Motoshi

AU - Murakami, Masahiro

PY - 2011/3/18

Y1 - 2011/3/18

N2 - 1,2,3-Benzotriazin-4(3H)-ones and 1,2,3,4-benzothiatriazine 1,1(2H)-dioxide reacted with isocyanides in the presence of a palladium catalyst to give 3-(imino)isoindolin-1-ones and 3-(imino)thiaisoindoline 1,1-dioxides, respectively, in high yield. An intermediate azapalladacycle was generated through denitrogenation of the triazine moiety, and an isocyanide was incorporated therein.

AB - 1,2,3-Benzotriazin-4(3H)-ones and 1,2,3,4-benzothiatriazine 1,1(2H)-dioxide reacted with isocyanides in the presence of a palladium catalyst to give 3-(imino)isoindolin-1-ones and 3-(imino)thiaisoindoline 1,1-dioxides, respectively, in high yield. An intermediate azapalladacycle was generated through denitrogenation of the triazine moiety, and an isocyanide was incorporated therein.

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DO - 10.1021/ol103143a

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JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

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ER -

Palladium-catalyzed denitrogenation reaction of 1,2,3-benzotriazin-4(3 H)-ones incorporating isocyanides

Abstract

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