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Synlett 2007(10): 1610-1612  
DOI: 10.1055/s-2007-982540
LETTER
© Georg Thieme Verlag Stuttgart · New York

A Novel Synthesis of Aminofurans Using a Four-Component Reaction

Abdolali Alizadeh*, Sadegh Rostamnia, Nasrin Zoreh, Qasem Oskueyan
Department of Chemistry, Tarbiat Modarres University, P.O. Box 14155-175, Tehran, Iran
Fax: +98(21)88006544; e-Mail: aalizadeh@modares.ac.ir; e-Mail: abdol_alizad@yahoo.com;
Further Information

Publication History

Received 2 February 2007
Publication Date:
06 June 2007 (online)

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Abstract

Protonation of the reactive intermediate produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates by carboxylic acid leads to vinylphosphonium salts, which undergo nucleophilic reaction with carboxylate anion to ­produce dialkyl (E)-2-aroyl-2-butenedioate. This intermediate is trapped with isocyanide to produce dialkyl 2-(alkylamino)-5-(aryl)-3,4-furandicarboxylate.

Key words

alkyl isocyanide - dialkyl acetylenedicarboxylate - carboxylic acid - multicomponent reaction - triphenylphosphine

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29

To a magnetically stirred solution of 4-nitrobenzoic acid (0.17 g, 1 mmol) and dimethyl acetylenedicarboxylate (0.14 g, 1 mmol) in anhyd CH2Cl2 (5 mL) was added dropwise a solution of triphenylphosphine (0.26 g, 1 mmol) and tert-butyl isocyanide (0.83 g, 1 mmol) in anhyd CH2Cl2 (3 mL) at r.t. over 20 min. The reaction mixture was stirred for 24 h. The solvent was removed under reduced pressure, and the residue was separated by silica gel (Merck 230-240 mesh) column chromatography using hexane-EtOAc mixture as eluent. The product 4a was obtained as orange crystals; yield: 74% (0.28 g); mp 177-179 °C. IR (KBr): 3445 (NH), 1724 (CO2Me), 1669 (CO2Me), 1504, 1468 (Ar), 1591, 1326 (NO2), 1261, 1213, 1184, 1103 (CO) cm-1. 1H NMR (500.1 MHz, CDCl3): δ = 1.52 (s, 9 H, CMe3), 3.79 (s, 3 H, OMe), 3.96 (s, 3 H, OMe), 6.97 (s, 1 H, NH), 7.61 (d, 3 J HH = 8.9 Hz, 2 H, 2 × CH of Ar), 8.22 (d, 3 J HH = 8.9 Hz, 2 H, 2 × CH of Ar). 13C NMR: δ = 29.81 (CMe 3), 51.43 (CMe3), 53.03 (OMe), 53.13 (OMe), 89.65 (C3 of furan), 117.51 (C4 of furan), 123.95 (2 × CH of Ar), 124.40 (2 × CH of Ar), 134.99 (Cipso), 138.36 (CipsoNO2), 146.00 (C5 of furan), 161.94 (C2 of furan), 164.58 (CO2Me), 165.50 (CO2Me). MS: m/z (%) = 377 (10) [M+ + 1], 376 (30) [M+], 320 (100), 288 (78), 256 (19), 151 (71), 104 (35), 76 (21), 57 (81), 41 (66). Anal. Calcd for C18H20N2O7 (376.36): C, 57.44; H, 5.36; N, 7.44. Found: C, 58.00; H, 5.51; N, 7.52.