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DOI: 10.1055/s-0030-1259325
Synthesis of 2-Imino-3-aminobenzofurans via Multicomponent Reactions from TosMIC
Publication History
Publication Date:
19 January 2011 (online)
Abstract
A simple synthesis of 2-imino-3-aminobenzofurans was developed based on multicomponent reactions from p-toluenesulfonylmethylisocyanide, salicylaldehyde, and substituted anilines. The crystal structures of two of the aminobenzofurans were established by X-ray crystal structure analysis.
Key words
multicomponent reactions - imines - furans - TosMIC - isocyanide
- Supporting Information for this article is available online:
- Supporting Information
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References and Notes
General Procedure
for the Preparation of 2-Imino-3-aminobenzofurans
Salicylaldehyde 2 (2.00 mmol) was added to a solution of
the amines 3a-f (1.00
mmol) in MeOH (15 mL). The mixture was stirred for 30 min at r.t.
and p-toluenesulfonylmethyl isocyanide
(4, 1.20 mmol) was added. The reaction
mixture was refluxed (3-24 h), and the solid precipitate
was collected by filtration and washed with hexane.
Selected Data for Compound 5a
The
product 5a (0.450 g) was obtained as a
red solid in 61% yield, mp 253-255 ˚C.
IR: 3366 (OH), 1595 (C=N), 1310, 1275, 744 cm-¹. ¹H
NMR (400 MHz, DMSO-d
6): δ = 11.52 (1
H, br s, OH), 10.78 (1 H, br s, OH), 8.98 (1 H, s, H-7), 8.44 (1
H, br s, NH), 7.71-7.67 (2 H, m, ArH), 7.60-7.56
(2 H, m, ArH), 7.42-7.32 (3 H, m, ArH), 7.24 (1 H, t, J = 7.6 Hz, ArH),
6.93-6.87 (2 H, m, ArH), 6.61 (1 H, d, J = 9.04
Hz, ArH). ¹³C NMR (100 MHz, DMSO-d
6): δ = 160.0,
156.2 (C=N), 151.0, 147.4, 144.8, 141.7, 138.4, 134.1,
132.1, 126.7, 126.4, 123.7, 120.7 (2 C), 120.1, 117.9, 117.2, 114.5, 111.9,
111.7, 109.2. MS (20 eV): m/z (%) = 389
(100) [M]+, 372 (16), 342
(8), 268 (27), 236 (13), 211 (25), 122 (38). HRMS: m/z calcd
for C21H16N3O5 [M+ + H]+:
390.1084; found: 390.1083.
Crystallographic data: Single crystal X-ray diffraction studies were realized on a KAPPA CCD diffractometer. Solution and refinement: direct methods SHELXS-86²0 and SIR-2004²¹ for structure solution and the SHELXL-97²² software package for refinement and data output. For compounds 5a and 5c full crystallographic data were submitted as CIF files with the Cambridge Crystallographic Data Centre, CCDC Nos. 750840 for 5a and 750841 for 5c.