Copper(II) Acetate Mediated Synthesis of 3-Sulfonyl-2-aryl-2H-chromenes

Meng-Yang Chang; Yu-Hsin Chen; Han-Yu Chen

doi:10.1055/s-0039-1689973

Synthesis, Table of Contents

Synthesis 2019; 51(18): 3419-3430
DOI: 10.1055/s-0039-1689973

paper

Copper(II) Acetate Mediated Synthesis of 3-Sulfonyl-2-aryl-2H-chromenes

Authors

Meng-Yang Chang *

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan, ROC

^bDepartment of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan, ROC Email: mychang@kmu.edu.tw
Yu-Hsin Chen

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan, ROC
Han-Yu Chen

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan, ROC

Abstract

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Abstract

This paper describes a concise, easy-operation, high-yielding method for the synthesis of 3-sulfonyl-2-aryl-2H-chromenes by a one-pot, straightforward two-step synthetic route, which includes (i) Cu(OAc)₂/PyBOP-mediated intermolecular [4+2] annulation of substituted salicylic acids with β-sulfonylstyrenes in the presence of DMAP in refluxing DMF, and (ii) sequential O-alkylation of the resulting sulfonylflavanones with n-butyl bromide. A plausible mechanism is proposed and discussed. This protocol provides a highly effective annulation via one carbon–oxygen (C–O) and one carbon–carbon (C–C) bond formations.

Key words

copper(II) acetate - 2-aryl-2H-chromenes - salicylic acids - β-sulfonylstyrenes - intermolecular [4+2] annulation

Full Text

References

References

For reviews on the synthesis of chromenes, see:

1a Majumdar N, Paul ND, Mandal S, de Bruin B, Wulff WD. ACS Catal. 2015; 5: 2329
1b Shi Y.-L, Shi M. Org. Biomol. Chem. 2007; 5: 1499
1c Ferreira SB, da Silva FC, Pinto AC, Gonzaga DT. G, Ferreira VF. J. Heterocycl. Chem. 2009; 46: 1080
1d Ellis GP, Lockhart IM. In The Chemistry of Heterocyclic Compounds: Chromenes, Chromanones, and Chromones, Vol. 31. Ellis GP. Wiley-VCH; New York: 2009: 1-196

Biological activities of 2-aryl-2H-chromenes. For candenatenin E, see:

2a Cheenpracha S, Karalai C, Ponglimanont C, Kanjana-Opas A. J. Nat. Prod. 2009; 72: 1395

For hilgartene, see:

2b Gómez-Garibay F, Calderón JS, De La O Arciniega M, Céspedes CL, Téllez-Valdés O, Taboada J. Phytochemistry 1999; 52: 1159

For acolbifene, see:

2c Gauthier S, Caron B, Cloutier J, Dory YL, Farve A, Larouche D, Mailhot J, Ouellet C, Schwerdtfeger A, Leblanc G, Martel C, Simard J, Mérand Y, Bélanger A, Labrie C, Labrie F. J. Med. Chem. 1997; 40: 2117

For photochromism of 2,2-diaryl-2H-chromenes, see:

3a Queiroz M.-JR. P, Abreu AS, Ferreira PM. T, Oliveira MM, Dubest R, Aubard J, Samat A. Org. Lett. 2005; 7: 4811
3b Moorthy JN, Venkatakrishnan P, Samanta S, Kumar DK. Org. Lett. 2007; 9: 919
3c Berdnikova DV, Paululat T, Jonusauskas G, Peregudova SM, Fedorova OA. Org. Lett. 2017; 19: 5633 ; and references cited therein

For general syntheses of 2-aryl-2H-chromenes, see:

4a Clark-Lewis JW, Jemison RW. Aust. J. Chem. 1968; 21: 2247
4b Cushman M, Nagarathnam D. J. Med. Chem. 1991; 34: 798

Organocatalyst-mediated syntheses of 2-aryl-2H-chromenes. For THT, see:

5a Ye L.-W, Sun X.-L, Zhu C.-Y, Tang Y. Org. Lett. 2006; 8: 3853

For amines, see:

5b Wang Q, Finn MG. Org. Lett. 2000; 2: 4063

For Brønsted acids, see:

5c Moquist PN, Kodama T, Schaus SE. Angew. Chem. Int. Ed. 2010; 49: 7096

For BF₃·OEt₂, see:

5d Doodeman R, Rutjes FP. J. T, Hiemstra H. Tetrahedron Lett. 2000; 41: 5979
5e Gil-Negrete JM, Sestelo JP, Sarandeses LA. Org. Lett. 2016; 18: 4316

Transition-metal-mediated syntheses of 2-aryl-2H-chromenes. For Co(II), see:

6a Paul ND, Mandal S, Otte M, Cui X, Zhang XP, de Bruin B. J. Am. Chem. Soc. 2014; 136: 1090

For Ru(II), see:

6b Hardouin C, Burgaud L, Valleix A, Doris E. Tetrahedron Lett. 2003; 44: 435
6c He H, Ye K.-Y, Wu Q.-F, Dai L.-X, You S.-L. Adv. Synth. Catal. 2012; 354: 1084

For Ni(0), see:

6d Graham TJ. A, Doyle AG. Org. Lett. 2012; 14: 1616

For Ga(III), see:

6e Yadav JS, Reddy BV. S, Biswas SK, Sengupta S. Tetrahedron Lett. 2009; 50: 5798

For Fe(III), see:

6f Calmus L, Corbu A, Cossy J. Adv. Synth. Catal. 2015; 357: 1381

For Pd(II), see:

6g Zeng B.-S, Yu X, Siu PW, Scheidt KA. Chem. Sci. 2014; 5: 2277
6h Jiang Z.-Z, Gao A, Li H, Chen D, Ding C.-H, Xu B, Hou X.-L. Chem. Asian J. 2017; 12: 3119
6i Xia Y, Xia Y, Zhang Y, Wang J. Org. Biomol. Chem. 2014; 12: 9333

For water-mediated syntheses of 2-aryl-2H-chromenes, see:

7a Zhang F.-Z, Tian Y, Li G.-X, Qu J. J. Org. Chem. 2015; 80: 1107
7b Candeias NR, Veiros LF, Afonso CA. M, Gois PM. P. Eur. J. Org. Chem. 2009; 1859

Synthetic applications of 2-aryl-2H-chromenes. For dimerization, see:

8a Luan Y, Sun H, Schaus SE. Org. Lett. 2011; 13: 6480
8b Devakaram R, Black D, Kumar N. Tetrahedron Lett. 2010; 51: 3636

For flavones, see:

8c Banerjee D, Kayal U, Maiti G. Tetrahedron Lett. 2016; 57: 1667

For dihydrochalcones, see:

8d Maiti G, Kayal U, Karmakar R, Bhattacharya RN. Tetrahedron Lett. 2012; 53: 6321

For cyclopropanations, see:

8e Stokes S, Mustain R, Pickle L, Mead KT. Tetrahedron Lett. 2012; 53: 3890

9a Chang M.-Y, Wu Y.-S, Hsiao Y.-T. Synthesis 2018; 50: 4651
9b Chang M.-Y, Chen Y.-H, Wang H.-S. J. Org. Chem. 2018; 83: 2361

Domino oxa-Michael/aldol condensation. For a 3-formyl group, see:

10a Climent MJ, Iborra S, Sabater MJ, Vidal JD. Appl. Catal., A 2014; 481: 27
10b Shen H, Yang K.-F, Shi Z.-H, Jiang J.-X, Lai G.-Q, Xu L.-W. Eur. J. Org. Chem. 2011; 5031

For a 3-nitro group, see:

10c Liu S.-X, Jia C.-M, Yao B.-Y, Chen X.-L, Zhang Q. Synthesis 2016; 48: 407

11a Bauer DJ, Selway JW. T, Batchelor JF, Tisdale M, Caldwell IC, Young DA. B. Nature 1981; 292: 369
11b Cheng J.-F, Ishikawa A, Ono Y, Arrhenius T, Zadzan A. Bioorg. Med. Chem. Lett. 2003; 13: 3647

12 CCDC 1811124 (4a), CCDC 1835628 (6b), CCDC 1835629 (6q), CCDC 1835630 (6x), CCDC 1835631 (6y), CCDC 1835632 (6z), CCDC 1835633 (6ab), and CCDC 1842006 (6aj) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.

For the complexation of Cu(II) with salicylic acids, see:

13a Chen H.-J, Lin Z.-Y, Li M.-Y, Lian R.-J, Xue Q.-W, Chung J.-L, Chen S.-C, Chen Y.-J. Tetrahedron 2010; 66: 7755
13b Lin CJ, Zheng YQ, Zhang DY, Xu W. Russ. J. Coord. Chem. 2014; 40: 932

14a Shaikh M, Atyam KK, Sahu M, Ranganath KV. S. Chem. Commun. 2017; 53: 6029
14b Ren X, Han C, Feng X, Du H. Synlett 2017; 28: 2421

Supplementary Material