1,4-Diazabicyclo[2.2.2]octane-Catalyzed Multicomponent Domino Strategy for the Synthesis of Tetrasubstituted NH-Pyrroles

Xiangqing Chang; Xiaofeng Yang; Zhiwei Chen; Weihui Zhong

doi:10.1055/s-0037-1611857

Synlett, Table of Contents

Synlett 2019; 30(12): 1431-1436
DOI: 10.1055/s-0037-1611857

letter

1,4-Diazabicyclo[2.2.2]octane-Catalyzed Multicomponent Domino Strategy for the Synthesis of Tetrasubstituted NH-Pyrroles

Xiangqing Chang

,

Xiaofeng Yang

,

Zhiwei Chen *

College of Pharmaceutical Sciences, Zhejiang University of Technology China and Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P. R. of China Email: chenzhiwei@zjut.edu.cn Email: weihuizhong@zjut.edu.cn

,

Weihui Zhong*

› Author Affiliations

Abstract

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Abstract

A mild and efficient 1,4-diazabicyclo[2.2.2]octane (DABCO)-catalyzed three-component domino reaction was developed for the synthesis of highly functionalized NH-pyrroles from arylglyoxal monohydrates, enamino esters, and cyclic 1,3-dicarbonyl compounds in 1,4-dioxane at room temperature for 0.5 hours. Various substituted NH-pyrroles were obtained in moderate to good yields.

Key words

multicomponent reaction - pyrroles - DABCO - cyclization - arylglyoxal monohydrates - enamino esters

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References

References and Notes

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12 Ethyl 4-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-2,5-diphenyl-1H-pyrrole-3-carboxylate (4a); Typical ProcedureA mixture of the 4-hydroxycoumarin (1a; 1 mmol), phenylglyoxal monohydrate (2a; 1 mmol), β-enamino ester 3a (1 mmol), and DABCO (10 mol%) in 1,4-dioxane (5 mL) was stirred at the reflux for 0.5 h. Upon completion of the reaction, the mixture was cooled to r.t. and aq NH₄Cl (30 mL) was added. The aqueous phase was extracted with EtOAc (3 × 25 mL). The combined organic extracts were dried (Na₂SO₄), filtered, and concentrated in vacuo. The residue was purified by column chromatography (silica gel, DCM-MeOH (160:1 v/v)) to give a pale white powder; yield: 338 mg (75%); mp = 209–211 °C.1H NMR (600 MHz, DMSO-d6): δ = 11.88 (s, 1H), 10.94 (s, 1H), 7.85 (d, J = 8.4 Hz, 1H), 7.64 –7.62 (m, 3H), 7.48–7.45 (m, 4H), 7.43–7.38 (m, 2H), 7.35 (t, J = 7.2 Hz, 1H), 7.31 (t, J = 7.2 Hz, 2H), 7.20 (t, J = 7.2 Hz, 1H), 3.93–3.83 (m, 2H), 0.81 (t, J = 7.2 Hz, 3H). ¹³C NMR (150 MHz, DMSO-d ₆): δ = 164.5, 162.6, 161.2, 152.9, 138.0, 132.6, 132.5, 132.4, 132.2, 130.0, 128.8, 128.2, 128.1, 127.4, 127.1, 124.3, 124.0, 116.7, 116.5, 113.4, 112.4, 101.8, 59.1, 14.0. MS (ESI): m/z = 450 [M – H]^–. HRMS-ESI: m/z [M – H]^– calcd for C₂₈H₂₀NO₅: 450.1347; found: 450.1350.

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