Synlett 2013; 24(6): 713-718
DOI: 10.1055/s-0032-1318392
letter
© Georg Thieme Verlag Stuttgart · New York

Silicon-Induced General, Mild, and Efficient One-Pot, Three-Component Synthesis of Amidoalkyl Naphthol Libraries

Tarek A. Salama
a   Chemistry Department, Faculty of Science, Mansoura University, 35516 Mansoura, Egypt    Fax: +20(50)2246781   Email: tasalama@yahoo.com
b   Division of Organic Chemistry, National Chemical Laboratory, Pune 411008, India
› Author Affiliations
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.

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 46 and 2:1 for 710) as eluent to give pure 1-amidoalkyl naphthols. Compounds 6ad 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.