Synthesis of fused isoquinolinone and iminoisoindolinone derivatives via a copper-catalyzed regioselective switching process

Veerababurao Kavala, Cheng Chuan Wang, Yu Hsuan Wang, Chun Wei Kuo, Donala Janreddy, Wen Chang Huang, Ting Shen Kuo, Chiu Hui He, Mei Ling Chen, Ching-Fa Yao

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Copper-catalyzed base switching procedures for the synthesis of various fused isoquinolinone derivatives and iminoisoindolinone derivatives from the same starting materials have been developed. In these reaction sequences it is found that benzyl cyanide acts as a nucleophile in the presence of strong bases while it acts as a cyanide donor in the presence of weak bases. A wide substrate scope, good functional group tolerance, and handy reaction conditions are the important features of these protocols. Futhermore, using these protocols a wide variety of imidazolone-fused isoquinolinone derivatives, pyrimidinone-fused isoquinolinone derivatives, a diazapinone-fused isoquinolinone derivative and iminoisoindolinone derivatives were accessed in excellent to moderate yields.

Original languageEnglish
Pages (from-to)2609-2626
Number of pages18
JournalAdvanced Synthesis and Catalysis
Volume356
Issue number11-12
DOIs
Publication statusPublished - 2014 Aug 11

Fingerprint

Copper
Derivatives
Cyanides
Pyrimidinones
Nucleophiles
Functional groups
Substrates

Keywords

  • copper catalysts
  • fused isoquinolinones
  • iminoisoindolinones
  • regioselective switching

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Synthesis of fused isoquinolinone and iminoisoindolinone derivatives via a copper-catalyzed regioselective switching process. / Kavala, Veerababurao; Wang, Cheng Chuan; Wang, Yu Hsuan; Kuo, Chun Wei; Janreddy, Donala; Huang, Wen Chang; Kuo, Ting Shen; He, Chiu Hui; Chen, Mei Ling; Yao, Ching-Fa.

In: Advanced Synthesis and Catalysis, Vol. 356, No. 11-12, 11.08.2014, p. 2609-2626.

Research output: Contribution to journalArticle

Kavala, V, Wang, CC, Wang, YH, Kuo, CW, Janreddy, D, Huang, WC, Kuo, TS, He, CH, Chen, ML & Yao, C-F 2014, 'Synthesis of fused isoquinolinone and iminoisoindolinone derivatives via a copper-catalyzed regioselective switching process', Advanced Synthesis and Catalysis, vol. 356, no. 11-12, pp. 2609-2626. https://doi.org/10.1002/adsc.201301105
Kavala, Veerababurao ; Wang, Cheng Chuan ; Wang, Yu Hsuan ; Kuo, Chun Wei ; Janreddy, Donala ; Huang, Wen Chang ; Kuo, Ting Shen ; He, Chiu Hui ; Chen, Mei Ling ; Yao, Ching-Fa. / Synthesis of fused isoquinolinone and iminoisoindolinone derivatives via a copper-catalyzed regioselective switching process. In: Advanced Synthesis and Catalysis. 2014 ; Vol. 356, No. 11-12. pp. 2609-2626.
@article{378ee228d9d44b719f3ae5186a86a85c,
title = "Synthesis of fused isoquinolinone and iminoisoindolinone derivatives via a copper-catalyzed regioselective switching process",
abstract = "Copper-catalyzed base switching procedures for the synthesis of various fused isoquinolinone derivatives and iminoisoindolinone derivatives from the same starting materials have been developed. In these reaction sequences it is found that benzyl cyanide acts as a nucleophile in the presence of strong bases while it acts as a cyanide donor in the presence of weak bases. A wide substrate scope, good functional group tolerance, and handy reaction conditions are the important features of these protocols. Futhermore, using these protocols a wide variety of imidazolone-fused isoquinolinone derivatives, pyrimidinone-fused isoquinolinone derivatives, a diazapinone-fused isoquinolinone derivative and iminoisoindolinone derivatives were accessed in excellent to moderate yields.",
keywords = "copper catalysts, fused isoquinolinones, iminoisoindolinones, regioselective switching",
author = "Veerababurao Kavala and Wang, {Cheng Chuan} and Wang, {Yu Hsuan} and Kuo, {Chun Wei} and Donala Janreddy and Huang, {Wen Chang} and Kuo, {Ting Shen} and He, {Chiu Hui} and Chen, {Mei Ling} and Ching-Fa Yao",
year = "2014",
month = "8",
day = "11",
doi = "10.1002/adsc.201301105",
language = "English",
volume = "356",
pages = "2609--2626",
journal = "Advanced Synthesis and Catalysis",
issn = "1615-4150",
publisher = "Wiley-VCH Verlag",
number = "11-12",

}

TY - JOUR

T1 - Synthesis of fused isoquinolinone and iminoisoindolinone derivatives via a copper-catalyzed regioselective switching process

AU - Kavala, Veerababurao

AU - Wang, Cheng Chuan

AU - Wang, Yu Hsuan

AU - Kuo, Chun Wei

AU - Janreddy, Donala

AU - Huang, Wen Chang

AU - Kuo, Ting Shen

AU - He, Chiu Hui

AU - Chen, Mei Ling

AU - Yao, Ching-Fa

PY - 2014/8/11

Y1 - 2014/8/11

N2 - Copper-catalyzed base switching procedures for the synthesis of various fused isoquinolinone derivatives and iminoisoindolinone derivatives from the same starting materials have been developed. In these reaction sequences it is found that benzyl cyanide acts as a nucleophile in the presence of strong bases while it acts as a cyanide donor in the presence of weak bases. A wide substrate scope, good functional group tolerance, and handy reaction conditions are the important features of these protocols. Futhermore, using these protocols a wide variety of imidazolone-fused isoquinolinone derivatives, pyrimidinone-fused isoquinolinone derivatives, a diazapinone-fused isoquinolinone derivative and iminoisoindolinone derivatives were accessed in excellent to moderate yields.

AB - Copper-catalyzed base switching procedures for the synthesis of various fused isoquinolinone derivatives and iminoisoindolinone derivatives from the same starting materials have been developed. In these reaction sequences it is found that benzyl cyanide acts as a nucleophile in the presence of strong bases while it acts as a cyanide donor in the presence of weak bases. A wide substrate scope, good functional group tolerance, and handy reaction conditions are the important features of these protocols. Futhermore, using these protocols a wide variety of imidazolone-fused isoquinolinone derivatives, pyrimidinone-fused isoquinolinone derivatives, a diazapinone-fused isoquinolinone derivative and iminoisoindolinone derivatives were accessed in excellent to moderate yields.

KW - copper catalysts

KW - fused isoquinolinones

KW - iminoisoindolinones

KW - regioselective switching

UR - http://www.scopus.com/inward/record.url?scp=84906283662&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84906283662&partnerID=8YFLogxK

U2 - 10.1002/adsc.201301105

DO - 10.1002/adsc.201301105

M3 - Article

AN - SCOPUS:84906283662

VL - 356

SP - 2609

EP - 2626

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4150

IS - 11-12

ER -