Copper-catalyzed multicomponent reactions for the efficient synthesis of diverse spirotetrahydrocarbazoles

In the presence of copper sulfate, three- or four-component reactions of 2-methylindole, aromatic aldehydes and various cyclic dienophiles in refluxing toluene afforded diverse spirotetrahydrocarbazoles. This reaction is an important development of the Levy reaction by using 2-methylindole to replac...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2022-07, Vol.18 (1), p.796-808
Main Authors: Zhan, Shao-Cong, Fang, Ren-Jie, Sun, Jing, Yan, Chao-Guo
Format: Article
Language:English
Subjects:
Acetic acid
Acids
Aldehydes
Carbazole
Chemistry
Copper
diels–alder reaction
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indole
indolo-2,3-quinodimethane
levy reaction
Pyrimidines
spirooxindole
tetrahydrocarbazole
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Summary:In the presence of copper sulfate, three- or four-component reactions of 2-methylindole, aromatic aldehydes and various cyclic dienophiles in refluxing toluene afforded diverse spirotetrahydrocarbazoles. This reaction is an important development of the Levy reaction by using 2-methylindole to replace ethyl indole-2-acetate and successfully provides facile access to important polysubstituted spiro[carbazole-3,3'-indolines], spiro[carbazole-2,3'-indolines], spiro[carbazole-3,5'-pyrimidines] and spiro[carbazole-3,1'-cycloalkanes] in satisfactory yields and with high diastereoselectivity.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.18.80