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Synlett 2016; 27(10): 1597-1601
DOI: 10.1055/s-0035-1561853
DOI: 10.1055/s-0035-1561853
letter
Base-Promoted Ecofriendly Synthesis of Trisubstituted Pyrazoles from α,β-Alkynyl N-Tosylhydrazones under Metal- and Solvent-Free Conditions
Further Information
Publication History
Received: 16 January 2016
Accepted after revision: 26 February 2016
Publication Date:
16 March 2016 (online)
![](https://www.thieme-connect.de/media/synlett/201610/lookinside/thumbnails/st-2016-w0032-l_10-1055_s-0035-1561853-1.jpg)
Abstract
A simple and green method is described for the synthesis of trisubstituted pyrazoles from α,β-alkynyl N-tosylhydrazones under metal- and solvent-free conditions. Notably, only diisopropylamine is required as a promoter, and the reaction can be easily performed at room temperature and on a gram scale.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561853.
- Supporting Information
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- 18 Pyrazoles 2; General Procedure i-Pr2NH (0.6 mmol) and the appropriate N-tosylhydrazone 1 (0.3 mmol) were thoroughly ground with a pestle and mortar for 30 min. When the reaction was complete, the mixture was purified by crystallization from CH2Cl2 or by column chromatography (silica gel, EtOAc–PE) to give the pure pyrazole product 2. 3,5-Diphenyl-1-tosyl-1H-pyrazole (2a) White solid; yield: 103 mg (92%; gram scale: 81%); mp 122–124 °C. IR (KBr): 3029, 2921, 2855, 1594, 1558, 1459, 1382, 1195, 1177, 761, 660, 598 cm–1. 1H NMR (500 MHz, CDCl3): δ = 2.35 (s, 3 H), 6.60 (s, 1 H), 7.19 (d, J = 8.0 Hz, 2 H), 7.35–7.45 (m, 8 H), 7.62 (d, J = 8.0 Hz, 2 H), 7.84 (d, J = 7.0 Hz, 2 H). 13C NMR (125 MHz, CDCl3): δ = 21.69, 109.54, 126.48, 127.84, 128.04, 128.72, 129.33, 129.49, 129.62, 129.67, 130.02, 131.37, 134.88, 145.35, 149.48, 155.21. HRMS (ESI): m/z [M + H]+ calcd for C22H19N2O2S: 375.1167; found: 375.1161.
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