Ansari, Arshad J. ; Wani, Aabid Abdullah ; Maurya, Antim K. ; Verma, Sarika ; Agnihotri, Vijai K. ; Sharon, Ashoke ; Bharatam, Prasad V. ; Sawant, Devesh M. (2019) An unprecedented N- to C-sulfonyl migration in the reaction of azomethine amine and allenoates: access to arylsulfonylmethyl substituted pyrazolo[1,5-c]quinazoline and mechanistic studies Chemical Communications, 55 (98). pp. 14825-14828. ISSN 1359-7345
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Official URL: http://doi.org/10.1039/C9CC06751E
Related URL: http://dx.doi.org/10.1039/C9CC06751E
Abstract
A serendipitous discovery of [1,3]-sulfonyl migration has been made in the two-component reaction of azomethine imine and allenoates. Current methodology involving N–S bond cleavage and C–S bond formation provided easy access to biologically important arylsulfonylmethyl substituted pyrazolo[1,5-c]quinazolines. Subsequently, a one-pot sequential protocol has been developed from the easily available starting material. The mechanistic investigation using quantum chemical methods revealed that the sulfonyl migration step is a concerted [1,3]-sigmatropic shift.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Royal Society of Chemistry. |
| ID Code: | 116266 |
| Deposited On: | 12 Apr 2021 09:17 |
| Last Modified: | 12 Apr 2021 09:17 |
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