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- Title
Hypervalent Iodine(III)-Mediated Benzannulation of Enamines with Alkynes: an Efficient Synthesis of Substituted Aminonaphthoic Acid Derivatives.
- Authors
Peng Gao; Mingjin Fan; Zijing Bai; Yunyang Wei
- Abstract
An intermolecular two C--C bond formation procedure for the synthesis of carbocycles mediated by hypervalent iodine(III) reagents was developed. This metal free protocol provided a new approach for the synthesis of useful substituted 1-amino-2-naphthoic acid derivatives via benzannulation reactions. Various N-unsubstituted and N-alkyl substituted aromatic enamines with terminal alkynes and non-terminal alkynes can be converted into corresponding 1-amino-2-naphthoic acid derivatives under mild reaction conditions. When meta-substituted phenyl enamines were employed in the reaction, two cyclization paths were detected in the reaction and ortho-cyclization products were the only or major products. Good functional group tolerance, readily available material and high atom utilization efficiency make this method a potential procedure which may find broad application in organic synthesis.
- Subjects
IODINE compounds synthesis; CARBOCYCLIC compounds; SUBSTITUENTS (Chemistry); HYPERVALENCE (Theoretical chemistry); ALKYNE synthesis; CARBON-carbon bonds synthesis
- Publication
Chinese Journal of Chemistry, 2015, Vol 33, Issue 4, p479
- ISSN
1001-604X
- Publication type
Article
- DOI
10.1002/cjoc.201400802