Photo-Promoted\nConstruction of 3‑Spiro-2-sulfonylimino-indoline\nSkeletons via Cascade Reaction

The cascade reaction of 3-diazo-2-sulfonyliminoindolines\nand <i>N</i>-methoxymethyl-<i>N</i>-[(trimethylsilyl)methyl]benzylamines\ngenerates 2-sulfonylimino-1′,3′,4′,6′-tetrahydro-2’<i>H</i>-spiro[indoline-3,5′-pyrimidine] and spiro[indoline-3,3′-pyrrolidine]\nderivatives simultaneously under the catalysis of TFA and blue light\nirradiation. Their formation mechanisms were proposed on the basis\nof isotope-labeled experiments and HRMS analysis of the controlled\nexperiment mixture, showing new reaction pathways. The current reaction\nprovides a new strategy for the synthesis of biologically important\nspiro[indoline-3,3′-pyrrolidine]-2-one derivatives.

Publication Details

Journal
Figshare
Published
2024-12-25
DOI
https://doi.org/10.1021/acs.orglett.4c04288.s001
Primary Topic
History of Computing Technologies
Type
article
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Photo-Promoted\nConstruction of 3‑Spiro-2-sulfonylimino-indoline\nSkeletons via Cascade Reaction

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History of Computing Technologies
article

Photo-Promoted\nConstruction of 3‑Spiro-2-sulfonylimino-indoline\nSkeletons via Cascade Reaction

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Abstract

The cascade reaction of 3-diazo-2-sulfonyliminoindolines\nand <i>N</i>-methoxymethyl-<i>N</i>-[(trimethylsilyl)methyl]benzylamines\ngenerates 2-sulfonylimino-1′,3′,4′,6′-tetrahydro-2’<i>H</i>-spiro[indoline-3,5′-pyrimidine] and spiro[indoline-3,3′-pyrrolidine]\nderivatives simultaneously under the catalysis of TFA and blue light\nirradiation. Their formation mechanisms were proposed on the basis\nof isotope-labeled experiments and HRMS analysis of the controlled\nexperiment mixture, showing new reaction pathways. The current reaction\nprovides a new strategy for the synthesis of biologically important\nspiro[indoline-3,3′-pyrrolidine]-2-one derivatives.

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History of Computing Technologies
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Photo-Promoted\nConstruction of 3‑Spiro-2-sulfonylimino-indoline\nSkeletons via Cascade Reaction · Figshare (2024) | TGRS Research Map | TGRS