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Chakraborty M, McConville DB, Koser GF, et al. A Novel High-Yield Synthesis of Substituted Isoindolequinones. J Org Chem. 1997;62(23):8193-8197doi: 10.1021/jo971671r.
Chakraborty, M., McConville, D. B., Koser, G. F., Tessier, C. A., Saito, T., Rinaldi, P. L., & Youngs, W. J. (1997). A Novel High-Yield Synthesis of Substituted Isoindolequinones. The Journal of organic chemistry, 62(23), 8193-8197. https://doi.org/10.1021/jo971671r
Chakraborty, Manisha, et al. "A Novel High-Yield Synthesis of Substituted Isoindolequinones." The Journal of organic chemistry vol. 62,23 (1997): 8193-8197. doi: https://doi.org/10.1021/jo971671r
Chakraborty M, McConville DB, Koser GF, Tessier CA, Saito T, Rinaldi PL, Youngs WJ. A Novel High-Yield Synthesis of Substituted Isoindolequinones. J Org Chem. 1997 Nov 14;62(23):8193-8197. doi: 10.1021/jo971671r. PMID: 11671931.
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J Org Chem. 1997 Nov 14;62(23):8193-8197. doi: 10.1021/jo971671r.

A Novel High-Yield Synthesis of Substituted Isoindolequinones.

The Journal of organic chemistry

Manisha Chakraborty, David B. McConville, Gerald F. Koser, Claire A. Tessier, Takeshi Saito, Peter L. Rinaldi, Wiley J. Youngs

Affiliations

  1. Department of Chemistry, The University of Akron, Akron, Ohio 44325-3601.

PMID: 11671931 DOI: 10.1021/jo971671r

Abstract

The high-yield, general, one-pot synthesis of substituted isoindolequinones, a group of important radiosensitizers which sensitize hypoxic cells to the lethal effect of radiation in cancer radiotherapy, is described. Primary amines react with 2,3-bis[2-(trimethylsilyl)ethynyl]-5,6-dimethylhydroquinone (2) in methanol at room temperature under an inert atmosphere to give substituted isoindolequinones 2-alkyl-1,3,5,6-tetramethylisoindole-4,7-quinone (4) in almost quantitative yields. Moderate yields of 4 are also obtained using 2,3-diethynyl-5,6-dimethylhydroquinone (3) and amines as reactant and solvent under the similar conditions. Tris(2-aminoethyl)amine (TREN) reacts with 2 in MeOH/THF on reflux to produce the isoindolequinone derivative of TREN. Water with 2 on reflux in MeOH forms an isobenzofuranquinone. This indicates that the formation of similar heterocycles from small molecules (e.g., Group VA and VIA hydrides) and 2 is likely. Readily synthesizable starting materials, ease of chromatographic isolation of the product, reaction generality, use of no catalyst, and cost-effective environmentally benign solvents such as MeOH/EtOH make this novel reaction simple and convenient.

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