Synthesis of Functionalized Benzo[g]indoles and 1-Naphthols via Carbon-Carbon Triple Bond Breaking/Rearranging
Jia-Yin Wang1, Peng Zhou1,2, Guigen Li2,3
1School of Chemistry & Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou 221116, P. R. China.
Abstract:
Novel carbon-carbon triple bond breaking and rearranging reactions of benzene-linked allene-ynes have been established. The reactions can be selectively controlled toward the formation of two families of skeletally diverse benzo[g]indoles and 1-naphthols under mild conditions. Silver salt was found to efficiently promote indole annulation to give multifunctional benzo[g]indoles with the installation of two sulfonyl groups into the indole ring via N-S and N-F bond cleavage of NFSI, whereas NBS and NCS-mediated benzannulations occurred with the formation of dihalogenated 1-naphthols.
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