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DOI: 10.1055/s-0030-1261175
A Simple and Efficient Protocol to 1,2,4-Substituted Pyrroles via a Sonogashira Coupling-Acid-Catalyzed Cyclization
Publikationsverlauf
Publikationsdatum:
10. August 2011 (online)
Abstract
A facile and efficient protocol for the synthesis of 1,2,4-substituted pyrrole derivatives was developed. As a result of the ready availability of materials and the simple operation, this type of reaction should have potential utility in organic synthesis.
Key words
pyrroles - Sonogashira reaction - gallium triflate - cyclization - 2-bromoallylamine
- Supporting Information for this article is available online:
- Supporting Information (PDF)
- 1a
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References and Notes
General Procedure
for the Synthesis of 3a
To a solution of 1a (0.5 mmol) and 2a (0.6
mmol) in 5 mL of THF was charged CuI (2 mg. 0.01 mmol) and PdCl2(PPh3)2 (7
mg, 0.01 mmol), then charged 1 mL of Et3N under an N2 atmosphere
at r.t. The reaction was monitored by TLC until it went to completion
(4 h). The reaction mixture was quenched with H2O, extracted
with Et2O (30 mL), and dried over anhyd Na2SO4.
After evaporation of the Et2O, chromatography on silica
gel (PE) of the crude product afforded 3a. ¹H
NMR (400 MHz, CDCl3): δ = 7.35-7.32
(m, 4 H), 7.27-7.23 (m, 1 H), 6.52-6.52 (d, J = 0.8 Hz,
1 H), 6.01-6.00 (d, J = 2.0
Hz, 1 H), 3.84-3.81 (t, J = 7.4
Hz, 2 H), 2.12 (s, 3 H), 1.64-1.56 (m, 2 H), 1.23-1.17
(q, J = 7.5
Hz, 2 H), 0.83-0.79 (t, J = 7.4
Hz, 3 H). ¹³C NMR (100 MHz, CDCl3): δ = 134.6,
134.2, 129.1, 128.6, 126.9, 120.4, 118.7, 110.3, 47.0, 34.0, 20.2,
14.0, 12.2. IR (neat): 1491, 1342 cm-¹. HRMS: m/z calcd for C15H19N:
213.1517; found: 213.1518.