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Synfacts 2014; 10(10): 1029
DOI: 10.1055/s-0034-1379133
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Simple Synthesis of Substituted Polyheteroaromatic Compounds

Contributor(s):
Timothy M. Swager
,
Kathleen R. White
Jayakumar J, Parthasarathy K, Chen Y.-H, Lee T.-H, Chuang S.-C, * Cheng C.-H. * National Tsing Hua University and National Chiao Tung University, Hsinchu, Taiwan
One-Pot Synthesis of Highly Substituted Polyheteroaromatic Compounds by Rhodium(III)-Catalyzed Multiple C–H Activation and Annulation.

Angew. Chem. Int. Ed. 2014;
53: 9889-9892
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Publication History

Publication Date:
17 September 2014 (online)

 
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Key words

alkynes - annulation - benzamidines - C–H activation - rhodium

Significance

Highly substituted polyheteroaromatic compounds have attracted considerable interest for potential use as functional and luminescent materials. The authors report the one-pot synthesis of benzo(isoquinolino)naphthyridines by rhodium(III)-catalyzed multiple C–H activation and annulation starting from (Z)-N-hydroxybenzamidines and disubstituted alkynes. The reported compounds are obtained in high yields and can contain an array of substituents.


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Comment

The authors found that an intermediate product can be isolated after one alkyne addition, and that the intermediate product can be reacted with different alkynes to further vary the substituents on the final product 4. Interestingly, the method can also be applied to di(2-thienyl)-alkyne to give product 2 in 60% yield.


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