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Synlett 2017; 28(12): 1463-1466
DOI: 10.1055/s-0036-1588168
DOI: 10.1055/s-0036-1588168
letter
Novel One-Pot Cyclization of the Blaise Reaction Intermediate and Arylglyoxals: The Synthesis of Substituted NH-Pyrroles
Gefördert durch: We are grateful for financial support from the National Natural Science Foundation of China Grant / Award number ‘21276237’, ‘21676253’
Weitere Informationen
Publikationsverlauf
Received: 06. März 2017
Accepted after revision: 12. März 2017
Publikationsdatum:
11. April 2017 (online)
Abstract
A novel tandem Blaise reaction for the one-pot synthesis of substituted NH-pyrroles was described. The Blaise reaction intermediate, generated in situ from Reformatsky reagent and nitrile, reacted with arylglyoxals chemoselectively to afford a wide variety of substituted NH-pyrroles in good yields.
Key words
pyrroles - Blaise reaction intermediate - arylglyoxals - Reformatsky reagent - chromeno 4-hydroxy-1H-pyrroleSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588168.
- Supporting Information
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- 16 General Procedure for the One-Pot Synthesis of 4a To a stirred suspension of commercial zinc dust (1.26 g, 19.5 mmol) was added methanesulfonic acid (3.7 mg, 0.37 mmol) in anhydrous THF (20 mL). After 10 min of reflux, benzonitrile (1.0 g, 9.7 mmol) was added all at once. While maintaining reflux temperature, ethyl bromoacetate (2.43 g, 14.5 mmol) was added over 1 h with use of a syringe pump, and the reaction mixture was further heated at reflux for 1 h. The reaction mixture was cooled to r.t., and then arylglyoxal (1.62 g, 10.6 mmol) was added. After being stirred for 0.5 h at r.t., the reaction mixture was quenched with sat. aq NH4Cl at r.t. and extracted with EtOAc (3 × 30 mL). The combined organic layer was dried with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (EtOAc–hexane, 1:7 v/v) to afford product 4a (2.47 g, 8.0 mmol; 83%); light yellow solid, mp 156.6–157.4 °C. 1H NMR (400 MHz, DMSO-d 6): δ = 11.42 (s, 1 H), 8.68 (s, 1 H), 7.84 (dd, J = 8.4, 1.0 Hz, 2 H), 7.60–7.53 (m, 2 H), 7.46–7.30 (m, 5 H), 7.11 (t, J = 7.4 Hz, 1 H), 4.17 (q, J = 7.2 Hz, 2 H), 1.14 (t, J = 7.2 Hz, 3 H). 13C NMR (100 MHz, DMSO-d 6): δ = 165.83, 143.72, 132.94, 131.17, 130.99, 129.18, 127.80, 127.47, 126.99, 124.26, 123.36, 112.97, 59.23, 13.62. ESI-MS: m/z 308.1 [M + H]+. ESI-HRMS: m/z calcd for C19H17NO3 [M + H]+: 308.1253; found: 308.1258.