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Keywords:

  • domino reactions;
  • heterocycles;
  • oxidation;
  • rearrangement
Thumbnail image of graphical abstract

A novel cascade reaction involving oxidative dearomatization/semipinacol rearrangement of indol-2-yl cyclobutanols is explored with N-sulfonyloxaziridine (Davis oxaziridines) as oxidant, generating various 2-spiroquaternary 3-oxindoles in modest to good yields. This method might be useful in the synthesis of indole-based alkaloids bearing 2-spiroquaternary carbon centers. PTS=p-toluenesulfonic acid monohydrate.

Featured Compounds

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  1. 1 - 35
Compound 1a
Molecular Weight:201.2643
Molecular Formula:C13H15NO
InChIKey:FIQRXQDHXFKRAZ-UHFFFAOYSA-N
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Compound 3a
Molecular Weight:261.296
Molecular Formula:C13H11NO3S
InChIKey:MKHGVMIXRPGHOO-UHFFFAOYSA-N
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Compound 3b
Molecular Weight:275.323
Molecular Formula:C14H13NO3S
InChIKey:SYTQRZCKINWJKR-UHFFFAOYSA-N
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Compound 2a
Molecular Weight:215.2478
Molecular Formula:C13H13NO2
InChIKey:HHIFKMOWPHQXPW-UHFFFAOYSA-N
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Compound 3c
Molecular Weight:229.296
Molecular Formula:C10H15NO3S
InChIKey:GBBJBUGPGFNISJ-UPACWWRESA-N
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Compound 1b
Molecular Weight:215.2909
Molecular Formula:C14H17NO
InChIKey:XWBKEHIUENJYEZ-UHFFFAOYSA-N
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Compound 1c
Molecular Weight:259.3434
Molecular Formula:C16H21NO2
InChIKey:QGEHDXLTTIHMCB-UHFFFAOYSA-N
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Compound 2b
Molecular Weight:229.2744
Molecular Formula:C14H15NO2
InChIKey:SWCZCMFSWYMRKH-UHFFFAOYSA-N
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Compound 2c
Molecular Weight:273.327
Molecular Formula:C16H19NO3
InChIKey:ZOSVFMWZFBKSBR-UHFFFAOYSA-N
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Compound 2d
Molecular Weight:245.2738
Molecular Formula:C14H15NO3
InChIKey:SNVMTRMGCCQHHO-UHFFFAOYSA-N
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Compound 2e
Molecular Weight:245.2738
Molecular Formula:C14H15NO3
InChIKey:JKCFPNJZCKSTHE-UHFFFAOYSA-N
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Compound 2f
Molecular Weight:275.2998
Molecular Formula:C15H17NO4
InChIKey:KQOGINAQZSGILN-UHFFFAOYSA-N
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Compound 2g
Molecular Weight:249.693
Molecular Formula:C13H12ClNO2
InChIKey:HGGIRPXBJYXHMN-UHFFFAOYSA-N
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Compound 1h
Molecular Weight:277.3603
Molecular Formula:C19H19NO
InChIKey:LQVQWUIJJYBBDW-UWUNEBHHSA-N
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Compound 1i
Molecular Weight:321.4128
Molecular Formula:C21H23NO2
InChIKey:WZSWQWIZSIVCRJ-UEDWGHLCSA-N
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Compound 1j
Molecular Weight:255.3547
Molecular Formula:C17H21NO
InChIKey:SHACXMYDUUSBAO-UHFFFAOYSA-N
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Compound 1k
Molecular Weight:269.3813
Molecular Formula:C18H23NO
InChIKey:SDJPJLSREAGNRH-UHFFFAOYSA-N
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Compound 1l
Molecular Weight:283.4079
Molecular Formula:C19H25NO
InChIKey:AOCVYLJVRCRPHG-UHFFFAOYSA-N
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Compound 2h
Molecular Weight:291.3438
Molecular Formula:C19H17NO2
InChIKey:GDBMCBWFVJUZFY-KUHUBIRLSA-N
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Compound 2i
Molecular Weight:335.3963
Molecular Formula:C21H21NO3
InChIKey:JGVNIYOJFMCWAH-IERDGZPVSA-N
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Compound 2j
Molecular Weight:269.3383
Molecular Formula:C17H19NO2
InChIKey:CQSOPHSFEZNIKX-UHFFFAOYSA-N
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Compound 2k
Molecular Weight:283.3648
Molecular Formula:C18H21NO2
InChIKey:HSCVPQVUEWWPDB-UHFFFAOYSA-N
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Compound 2l
Molecular Weight:297.3914
Molecular Formula:C19H23NO2
InChIKey:BLXNOWADDJCCAR-UHFFFAOYSA-N
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Compound 1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 1d
Molecular Weight:231.2903
Molecular Formula:C14H17NO2
InChIKey:QWGOXTNJRBHIIB-UHFFFAOYSA-N
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Compound 1e
Molecular Weight:231.2903
Molecular Formula:C14H17NO2
InChIKey:OXNDWFPNVNEGDS-UHFFFAOYSA-N
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Compound 1f
Molecular Weight:261.3163
Molecular Formula:C15H19NO3
InChIKey:HOPDFQZAPVMRGB-UHFFFAOYSA-N
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Compound 1g
Molecular Weight:235.709
Molecular Formula:C13H14ClNO
InChIKey:YWNMHOIOTVNLAX-UHFFFAOYSA-N
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Compound 2
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 4
Molecular Weight:259.324
Molecular Formula:C14H13NO2S
InChIKey:HVCKVBQOKOFBFH-RVDMUPIBSA-N
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Compound 5
Molecular Weight:106.1219
Molecular Formula:C7H6O
InChIKey:HUMNYLRZRPPJDN-UHFFFAOYSA-N
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Compound 6
Molecular Weight:171.217
Molecular Formula:C7H9NO2S
InChIKey:LMYRWZFENFIFIT-UHFFFAOYSA-N
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Compound 1m
Molecular Weight:231.2903
Molecular Formula:C14H17NO2
InChIKey:RMMINCDRZPKGET-UHFFFAOYSA-N
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Compound 7m
Molecular Weight:474.571
Molecular Formula:C27H26N2O4S
InChIKey:JGFYDZBJEQQCBU-OHSXHVKISA-N
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Compound 9j
Molecular Weight:546.677
Molecular Formula:C31H34N2O5S
InChIKey:OYTYPAYSJXXWOA-QCENPCRXSA-N
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  1. 1 - 35