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Synlett 2013; 24(6): 713-718
DOI: 10.1055/s-0032-1318392
DOI: 10.1055/s-0032-1318392
letter
Silicon-Induced General, Mild, and Efficient One-Pot, Three-Component Synthesis of Amidoalkyl Naphthol Libraries
Further Information
Publication History
Received: 18 January 2013
Accepted after revision: 17 February 2013
Publication Date:
06 March 2013 (online)
Abstract
A general mild and efficient protocol for the synthesis of amidoalkyl naphthol libraries was achieved utilizing tetrachlorosilane and zinc chloride in dichloromethane at ambient temperature via a one-pot, three-component condensation of various aldehydes, nitriles (amides), and β-naphthol.
Key words
multicomponent reactions - amidoalkyl naphthols - tetrachlorosilane - Ritter reaction - combinatorial synthesisSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
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- 22 Typical Procedure for the MCR of Compounds 1–3 with SiCl4/ZnCl2 To a solution of anhyd ZnCl2 (0.7 g, 5 mmol) in CH2Cl2 (20 mL) were added aldehyde (5 mmol), 2-naphthol (5 mmol), and nitrile or amide (6.5 mmol). The reaction mixture was stirred at ambient temperature for 10 min, SiCl4 (1.2 mL, 10 mmol) was added, and the reaction mixture was stirred with exclusion of moisture. On completion (TLC monitoring of the progress of the reaction), the mixture was poured onto H2O (100 mL) and extracted with CH2Cl2 (2 × 50 mL). The combined organic extract was dried over anhyd MgSO4, evaporated, and the residue chromatographed on silica gel using PE–EtOAc (1:1 for 4–6 and 2:1 for 7–10) as eluent to give pure 1-amidoalkyl naphthols. Compounds 6a–d were isolated without chromatography in pure form by trituration with Et2O. Spectral data for representative (new) examples of 1-amidoalkyl naphthols are shown in the Supporting Information.