Catalyst‐Free One‐Pot Access to Pyrazoles and Disulfide‐Tethered Pyrazoles via Deamidative Heteroannulation of β‐Ketodithioesters with Semicarbazide Hydrochloride in Water
An operationally simple, mild, and catalyst‐free one‐pot protocol to access privileged pyrazoles and disulfide‐tethered pyrazoles has been devised by [3+2] heteroannulation of β‐ketodithioesters with semicarbazide hydrochloride in water under open air. The pH of the medium played a key role toward t...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2018-05, Vol.360 (9), p.1780-1785 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Koley, Suvajit Panja, Sumit Kumar Soni, Sonam Singh, Maya Shankar |
| description | An operationally simple, mild, and catalyst‐free one‐pot protocol to access privileged pyrazoles and disulfide‐tethered pyrazoles has been devised by [3+2] heteroannulation of β‐ketodithioesters with semicarbazide hydrochloride in water under open air. The pH of the medium played a key role toward the selectivity switch, as refluxing in water led to the formation of pyrazoles, whereas addition of sodium acetate in water enabled the formation of disulfide‐tethered pyrazoles. Notably, this protocol involves a tandem sequence of amination/cyclization/dehydration/hydrodesufurization/hydrolysis/deamidative reactions. A mechanistic rationale for this regio‐/chemoselective domino reaction is outlined, which is well supported and validated by density functional theory calculations. |
| doi_str_mv | 10.1002/adsc.201701595 |
| format | Article |
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The pH of the medium played a key role toward the selectivity switch, as refluxing in water led to the formation of pyrazoles, whereas addition of sodium acetate in water enabled the formation of disulfide‐tethered pyrazoles. Notably, this protocol involves a tandem sequence of amination/cyclization/dehydration/hydrodesufurization/hydrolysis/deamidative reactions. A mechanistic rationale for this regio‐/chemoselective domino reaction is outlined, which is well supported and validated by density functional theory calculations.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201701595</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Cascade chemical reactions ; Catalysis ; Catalysts ; Chemical reactions ; deamidation in water ; Dehydration ; Density functional theory ; density functional theory calculation ; disulfane ; Organic chemistry ; pH selective reaction ; Pyrazole ; Refluxing ; Sodium acetate</subject><ispartof>Advanced synthesis & catalysis, 2018-05, Vol.360 (9), p.1780-1785</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. 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| ispartof | Advanced synthesis & catalysis, 2018-05, Vol.360 (9), p.1780-1785 |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Cascade chemical reactions Catalysis Catalysts Chemical reactions deamidation in water Dehydration Density functional theory density functional theory calculation disulfane Organic chemistry pH selective reaction Pyrazole Refluxing Sodium acetate |
| title | Catalyst‐Free One‐Pot Access to Pyrazoles and Disulfide‐Tethered Pyrazoles via Deamidative Heteroannulation of β‐Ketodithioesters with Semicarbazide Hydrochloride in Water |
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