A copper-catalyzed Ritter-type cascade via iminoketene for the synthesis of quinazolin-4(3H)-ones and diazocines

Takumi Abe; Koshiro Kida; Koji Yamada

doi:10.1039/c7cc01406f

A copper-catalyzed Ritter-type cascade via iminoketene for the synthesis of quinazolin-4(3H)-ones and diazocines

Takumi Abe, Koshiro Kida, Koji Yamada

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

47 Citations (Scopus)

Abstract

We have developed a copper-catalyzed Ritter-type reaction/cyclization cascade of anthranilic acids and nitriles, affording the quinazolin-4(3H)-ones. The cascade proceeds through a Ritter-type reaction capturing the iminoketene intermediates by nitriles. Furthermore, we found a novel Ritter-type reaction/condensation/intramolecular anti-Markovnikov hydroamination cascade, providing access to functionalized diazocines in one-pot.

Original language	English
Pages (from-to)	4362-4365
Number of pages	4
Journal	Chemical Communications
Volume	53
Issue number	31
DOIs	https://doi.org/10.1039/c7cc01406f
Publication status	Published - 2017
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c7cc01406f

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abstract = "We have developed a copper-catalyzed Ritter-type reaction/cyclization cascade of anthranilic acids and nitriles, affording the quinazolin-4(3H)-ones. The cascade proceeds through a Ritter-type reaction capturing the iminoketene intermediates by nitriles. Furthermore, we found a novel Ritter-type reaction/condensation/intramolecular anti-Markovnikov hydroamination cascade, providing access to functionalized diazocines in one-pot.",

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AU - Kida, Koshiro

AU - Yamada, Koji

N1 - Funding Information: This work was financially supported by JSPS (KAKENHI Grant Number 16K18849 for T. A.) as a Grant-in-Aid for Young Scientists (B) and Hoyu Science Foundation (for T. A.). Publisher Copyright: © The Royal Society of Chemistry.

PY - 2017

Y1 - 2017

N2 - We have developed a copper-catalyzed Ritter-type reaction/cyclization cascade of anthranilic acids and nitriles, affording the quinazolin-4(3H)-ones. The cascade proceeds through a Ritter-type reaction capturing the iminoketene intermediates by nitriles. Furthermore, we found a novel Ritter-type reaction/condensation/intramolecular anti-Markovnikov hydroamination cascade, providing access to functionalized diazocines in one-pot.

AB - We have developed a copper-catalyzed Ritter-type reaction/cyclization cascade of anthranilic acids and nitriles, affording the quinazolin-4(3H)-ones. The cascade proceeds through a Ritter-type reaction capturing the iminoketene intermediates by nitriles. Furthermore, we found a novel Ritter-type reaction/condensation/intramolecular anti-Markovnikov hydroamination cascade, providing access to functionalized diazocines in one-pot.

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A copper-catalyzed Ritter-type cascade via iminoketene for the synthesis of quinazolin-4(3H)-ones and diazocines

Abstract

ASJC Scopus subject areas

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