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, Inhaltsverzeichnis

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*

› Institutsangaben

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 and Notes

1a De Souza JE. G, Dos Santos FL, Barros-Neto B, Dos Santos CG. De Melo C. P. Synth. Met. 2001; 119: 383
1b Walsh CT, Garneau-Tsodikova S, Howard-Jones AR. Nat. Prod. Rep. 2006; 23: 517
1c Ramanavičius A, Ramanavičienė A, Malinauskas A. Electrochim. Acta 2006; 51: 6025
1d Fan H, Peng J, Hamann MT, Hu J.-F. Chem. Rev. 2008; 108: 264
1e Young IS, Thornton PD, Thompson A. Nat. Prod. Rep. 2010; 27: 1801

2 Bhardwaj V, Gumber D, Abbot V, Dhiman S, Sharma P. RSC Adv. 2015; 5: 15233

3a Alberola A, González Ortega A, Sádaba ML, Sañudo C. Tetrahedron 1999; 55: 6555
3b Elghamry I. Synth. Commun. 2009; 39: 3010
3c Manley J, Kalman M, Conway B, Ball C, Havens J, Vaidyanathan R. J. Org. Chem. 2003; 68: 6447
3d Bellingham R, Carey J, Hussain N, Morgan D, Oxley P, Powling L. Org. Process Res. Dev. 2004; 8: 279

4a Minetto G, Raveglia L, Sega A, Taddei M. Eur. J. Org. Chem. 2005; 2005: 5277
4b Banik B, Samajdar S, Banik I. J. Org. Chem. 2004; 69: 213
4c Zhang L, Zhang J, Ma J, Cheng D.-J, Tan B. J. Am. Chem. Soc. 2017; 139: 1714
4d Handy S, Lavender K. Tetrahedron Lett. 2013; 54: 4377
4e Cranwell PB, O’Brien M, Browne DL, Koos P, Polyzos A, Peña-López M, Ley SV. Org. Biomol. Chem. 2012; 10: 5774
4f Chen J, Wu H, Zheng Z, Jin C, Zhang X, Su W. Tetrahedron Lett. 2006; 47: 5383

5a Matiychuk V, Martyak R, Obushak N, Ostapiuk Y, Pidlypnyi N. Chem. Heterocycl. Compd. (Engl. Transl.) 2004; 40: 1218
5b Trautwein A, Süßmuth R, Jung G. Bioorg. Med. Chem. Lett. 1998; 8: 2381
5c Estévez V, Villacampa M, Menéndez JC. Chem. Commun. 2013; 49: 591
5d Moss TA, Nowak T. Tetrahedron Lett. 2012; 53: 3056
5e Herath A, Cosford ND. P. Org. Lett. 2010; 12: 5182

6 Estévez V, Villacampa M, Menéndez JC. Chem. Soc. Rev. 2014; 43: 4633

7a Touré BB, Hall DG. Chem. Rev. 2009; 109: 4439
7b Dömling A, Wang W, Wang K. Chem. Rev. 2012; 112: 3083

8a Chang X, Zhang X, Chen Z. Org. Biomol. Chem. 2018; 16: 4279
8b Wang J, Zhou R, Zhuang S, Wu A. Tetrahedron 2019; 75: 1590
8c Eftekhari-Sis B, Zirak M, Akbari A. Chem. Rev. 2013; 113: 2958
8d Karamthulla S, Khan MN, Choudhury LH. RSC Adv. 2015; 5: 19724
8e Dhinakaran I, Padmini V, Bhuvanesh N. ACS Comb. Sci. 2016; 18: 236
8f Bunescu A, Wang Q, Zhu J. Org. Lett. 2014; 16: 1756
8g Ma G.-H, Jiang B, Tu X.-J, Ning Y, Tu S.-J, Li G. Org. Lett. 2014; 16: 4504

9a Lin W, Zheng Y.-X, Xun Z, Huang Z.-B, Shi D.-Q. ACS Comb. Sci. 2017; 19: 708
9b Wang H, Liu X, Feng X, Huang Z, Shi D. Green Chem. 2013; 15: 3307
9c Karamthulla S, Pal S, Khan MN, Choudhury LH. Synlett 2014; 25: 1926
9d Masoudi M, Anary-Abbasinejad M. Tetrahedron Lett. 2016; 57: 103

10 Yang X, Chen Z, Zhong W. Eur. J. Org. Chem. 2017; 2017: 2258

11a Chen Z, Bi J, Su W. Chin. J. Chem. 2012; 30: 1845
11b Naidu PS, Kolita S, Sharma M, Bhuyan PJ. J. Org. Chem. 2015; 80: 6381
11c Yang X, Zheng L, Chen Z, Zhong W. Synth. Commun. 2018; 48: 929
11d Jalani HB, Mali JR, Park H, Lee JK, Lee K, Lee K, Choi Y. Adv. Synth. Catal. 2018; 360: 4073

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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