Journal of Organic Chemistry p. 3404 - 3409 (1987)
Update date:2022-07-29
Topics:
Wenkert, Ernest
Moeller, Peter D. R.
Piettre, Serge R.
McPhail, Andrew T.
Grignard reagents from N-unsubstituted indoles and benzenesulfonyl chloride undergo reaction such as to produce unstable intermediates of β-chlorination and α-sulfonylation, which are transformed into oxindoles or substituted indoles.In the same reaction, yuehchukene (the naturally occurring dehydroprenylindole dimer) is converted into a spirooxindole, containing a strained four-membered ring, which is changed into a spirooxindole isomer with ring expansion on mild acid treatment.
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