Palladium-Catalyzed Cyclization Reaction of o-Haloanilines, CO2 and Isocyanides: Access to Quinazoline-2,4(1H,3H)-diones

Wen Zhen Zhang; Honglin Li; Yang Zeng; Xueyan Tao; Xiaobing Lu

doi:10.1002/cjoc.201700581

Palladium-Catalyzed Cyclization Reaction of o-Haloanilines, CO₂ and Isocyanides: Access to Quinazoline-2,4(1H,3H)-diones

Wen Zhen Zhang^*
, Honglin Li
, Yang Zeng
, Xueyan Tao
, Xiaobing Lu

^*Corresponding author for this work

Dalian University of Technology

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

34 Scopus citations

Abstract

Quinazoline-2,4(1H,3H)-diones are core structural subunits frequently found in many biologically important compounds. The reaction of 2-aminobenzonitrile and CO₂, which was frequently studied, only provided N3-unsubstituted quinazoline-2,4(1H,3H)-dione compounds. Herein we report palladium-catalyzed cyclization reactions of o-haloanilines, CO₂ and isocyanides to prepare N3-substituted quinazoline-2,4(1H,3H)-diones. Electron-rich o-bromoanilines participated in the cyclization reaction using Cs₂CO₃ at high temperature, and electron-deficient o-bromoaniline or o-iodoaniline substrates conducted the reaction using CsF as base to deliver corresponding quinazoline-2,4(1H,3H)-dione products in good yields.

Original language	English
Pages (from-to)	112-118
Number of pages	7
Journal	Chinese Journal of Chemistry
Volume	36
Issue number	2
DOIs	https://doi.org/10.1002/cjoc.201700581
State	Published - 1 Feb 2018
Externally published	Yes

Keywords

carbon dioxide fixation
homogeneous catalysis
isocyanide
nitrogen heterocycles
palladium

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10.1002/cjoc.201700581

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@article{663bb806e7204b31a611df0c00297412,

title = "Palladium-Catalyzed Cyclization Reaction of o-Haloanilines, CO2 and Isocyanides: Access to Quinazoline-2,4(1H,3H)-diones",

abstract = "Quinazoline-2,4(1H,3H)-diones are core structural subunits frequently found in many biologically important compounds. The reaction of 2-aminobenzonitrile and CO2, which was frequently studied, only provided N3-unsubstituted quinazoline-2,4(1H,3H)-dione compounds. Herein we report palladium-catalyzed cyclization reactions of o-haloanilines, CO2 and isocyanides to prepare N3-substituted quinazoline-2,4(1H,3H)-diones. Electron-rich o-bromoanilines participated in the cyclization reaction using Cs2CO3 at high temperature, and electron-deficient o-bromoaniline or o-iodoaniline substrates conducted the reaction using CsF as base to deliver corresponding quinazoline-2,4(1H,3H)-dione products in good yields.",

keywords = "carbon dioxide fixation, homogeneous catalysis, isocyanide, nitrogen heterocycles, palladium",

author = "Zhang, \{Wen Zhen\} and Honglin Li and Yang Zeng and Xueyan Tao and Xiaobing Lu",

note = "Publisher Copyright: {\textcopyright} 2018 SIOC, CAS, Shanghai, \& WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2018",

month = feb,

day = "1",

doi = "10.1002/cjoc.201700581",

language = "英语",

volume = "36",

pages = "112--118",

journal = "Chinese Journal of Chemistry",

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publisher = "John Wiley and Sons Inc",

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}

TY - JOUR

T1 - Palladium-Catalyzed Cyclization Reaction of o-Haloanilines, CO2 and Isocyanides

T2 - Access to Quinazoline-2,4(1H,3H)-diones

AU - Zhang, Wen Zhen

AU - Li, Honglin

AU - Zeng, Yang

AU - Tao, Xueyan

AU - Lu, Xiaobing

PY - 2018/2/1

Y1 - 2018/2/1

N2 - Quinazoline-2,4(1H,3H)-diones are core structural subunits frequently found in many biologically important compounds. The reaction of 2-aminobenzonitrile and CO2, which was frequently studied, only provided N3-unsubstituted quinazoline-2,4(1H,3H)-dione compounds. Herein we report palladium-catalyzed cyclization reactions of o-haloanilines, CO2 and isocyanides to prepare N3-substituted quinazoline-2,4(1H,3H)-diones. Electron-rich o-bromoanilines participated in the cyclization reaction using Cs2CO3 at high temperature, and electron-deficient o-bromoaniline or o-iodoaniline substrates conducted the reaction using CsF as base to deliver corresponding quinazoline-2,4(1H,3H)-dione products in good yields.

AB - Quinazoline-2,4(1H,3H)-diones are core structural subunits frequently found in many biologically important compounds. The reaction of 2-aminobenzonitrile and CO2, which was frequently studied, only provided N3-unsubstituted quinazoline-2,4(1H,3H)-dione compounds. Herein we report palladium-catalyzed cyclization reactions of o-haloanilines, CO2 and isocyanides to prepare N3-substituted quinazoline-2,4(1H,3H)-diones. Electron-rich o-bromoanilines participated in the cyclization reaction using Cs2CO3 at high temperature, and electron-deficient o-bromoaniline or o-iodoaniline substrates conducted the reaction using CsF as base to deliver corresponding quinazoline-2,4(1H,3H)-dione products in good yields.

KW - carbon dioxide fixation

KW - homogeneous catalysis

KW - isocyanide

KW - nitrogen heterocycles

KW - palladium

UR - https://www.scopus.com/pages/publications/85037974913

U2 - 10.1002/cjoc.201700581

DO - 10.1002/cjoc.201700581

M3 - 文章

AN - SCOPUS:85037974913

SN - 1001-604X

VL - 36

SP - 112

EP - 118

JO - Chinese Journal of Chemistry

JF - Chinese Journal of Chemistry

IS - 2

ER -

Palladium-Catalyzed Cyclization Reaction of o-Haloanilines, CO₂ and Isocyanides: Access to Quinazoline-2,4(1H,3H)-diones

Abstract

Keywords

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