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1-(2′-Anilinyl)prop-2-yn-1-ol Rearrangement for Oxindole Synthesis

Kothandaraman, Prasath ; Koh, Bing Qin ; Limpanuparb, Taweetham ; Hirao, Hajime ; Chan, Philip Wai Hong

Chemistry : a European journal, 2013-02, Vol.19 (6), p.1978-1985 [Periódico revisado por pares]

Weinheim: WILEY-VCH Verlag

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Título:
1-(2′-Anilinyl)prop-2-yn-1-ol Rearrangement for Oxindole Synthesis
Autor: Kothandaraman, Prasath ; Koh, Bing Qin ; Limpanuparb, Taweetham ; Hirao, Hajime ; Chan, Philip Wai Hong
Assuntos: alcohols ; Aniline Compounds - chemistry ; Catalysis ; Chemistry ; Cyclization ; Density functional theory ; Divergence ; domino reactions ; Indoles - chemical synthesis ; Indoles - chemistry ; Isomerization ; Mathematical analysis ; Migration ; Molecular Structure ; N-iodosuccinimide ; oxindoles ; Quantum Theory ; Relay ; Stereoisomerism ; Studies ; Succinimides - chemical synthesis ; Succinimides - chemistry ; Synthesis ; Transformations
É parte de: Chemistry : a European journal, 2013-02, Vol.19 (6), p.1978-1985
Notas: ark:/67375/WNG-J9BH7XBC-Z
Nanyang Technological University - No. 092 101 0053
A*STAR
ArticleID:CHEM201202606
istex:9A6903B8CF57AFC4E0F990DE8D8B89D7735041F2
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SourceType-Scholarly Journals-1
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content type line 23
Descrição: A synthetic method that relies on NIS (N‐iodosuccinimide)‐mediated cycloisomerization reactions of 1‐(2′‐anilinyl)prop‐2‐yn‐1‐ols to gem‐3‐(diiodomethyl)indolin‐2‐ones and 2‐(iodomethylene)indolin‐3‐ones has been developed. The reactions were shown to be chemoselective, with secondary and tertiary alcoholic substrates exclusively giving the 3‐ and 2‐oxindole products, respectively. In the case of the latter, the transformation features an unprecedented double 1,2‐OH and 1,2‐alkyl migration relay. Density functional theory (DFT) calculations based on proposed iodoaminocyclization species provide insight into this unique divergence in product selectivity. Alcohols to oxindoles: A chemoselective synthetic method that relies on NIS‐mediated cycloisomerization reactions of 1‐(2′‐anilinyl)prop‐2‐yn‐1‐ols to gem‐3‐(diiodomethyl)indolin‐2‐ones and 2‐(iodomethylene)indolin‐3‐ones was developed (see scheme; NIS=N‐iodosuccinimide). Secondary and tertiary alcoholic substrates exclusively gave the 3‐ and 2‐oxindole products, respectively; in the case of the latter, the transformation features an unprecedented double 1,2‐OH and 1,2‐alkyl migration relay.
Editor: Weinheim: WILEY-VCH Verlag
Idioma: Inglês

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1-(2′-Anilinyl)prop-2-yn-1-ol Rearrangement for Oxindole Synthesis

Kothandaraman, Prasath ; Koh, Bing Qin ; Limpanuparb, Taweetham ; Hirao, Hajime ; Chan, Philip Wai Hong

Weinheim: WILEY-VCH Verlag

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