Synthesis 2020; 52(20): 2979-2986
DOI: 10.1055/s-0040-1707205
paper
© Georg Thieme Verlag Stuttgart · New York

Application of Benzofuran-Derived Azadienes as Two-Carbon Building Blocks in Annulations: Chemo- and Diastereoselective Construction of Spiro-Benzofuran Scaffolds

Ye-Xin Wang
a  School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, P. R. of China   Email: fshi@jsnu.edu.cn   Email: wtan@jsnu.edu.cn
,
Yi-Nan Lu
a  School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, P. R. of China   Email: fshi@jsnu.edu.cn   Email: wtan@jsnu.edu.cn
,
Lin-Lin Xu
b  Key Lab of Environment and Health, School of Public Health, Xuzhou Medical University, Xuzhou 221006, P. R. of China   Email: xiaopangpeng@126.com
,
Feng-Tao Sheng
a  School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, P. R. of China   Email: fshi@jsnu.edu.cn   Email: wtan@jsnu.edu.cn
,
Jin-Peng Zhang
b  Key Lab of Environment and Health, School of Public Health, Xuzhou Medical University, Xuzhou 221006, P. R. of China   Email: xiaopangpeng@126.com
,
Wei Tan
a  School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, P. R. of China   Email: fshi@jsnu.edu.cn   Email: wtan@jsnu.edu.cn
,
Feng Shi
a  School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, P. R. of China   Email: fshi@jsnu.edu.cn   Email: wtan@jsnu.edu.cn
› Author Affiliations
We very much appreciate the financial support from National Natural Science Foundation of China (21772069 and 21831007), Six Kinds of Talents Project of Jiangsu Province (SWYY-025), TAPP, and Undergraduate Students Project of JSNU.
Further Information

Publication History

Received: 08 June 2020

Accepted after revision: 25 June 2020

Publication Date:
15 July 2020 (online)


§ These authors contributed equally to this work.

Abstract

A base-promoted (2+4) annulation of benzofuran-derived azadienes with para-quinone methide derivatives has been established, which afforded spiro-benzofuran derivatives in generally high yields (57–97%) and with good diastereoselectivities (85:15 to >95:5 dr). This reaction not only represents the first application of benzofuran-derived azadienes as two-carbon building blocks in annulations, but also provides an efficient protocol for the construction of spiro-benzofuran scaffolds with chemoselectivity and high diastereoselectivity. This approach will enrich the chemistry of benzofuran-derived azadiene-involved reactions.

Supporting Information

 
  • References


    • For some reviews:
    • 1a Kochanowska-Karamyan AJ, Hamann MT. Chem. Rev. 2010; 110: 4489
    • 1b Yu J, Shi F, Gong L.-Z. Acc. Chem. Res. 2011; 44: 1156
    • 1c Wu H, He Y.-P, Shi F. Synthesis 2015; 47: 1990
    • 1d Mei G.-J, Shi F. Chem. Commun. 2018; 54: 6607
    • 1e Wan Y, Li Y, Yan C, Yan M, Tang Z. Eur. J. Med. Chem. 2019; 183: 111691

      For some reviews:
    • 2a Mei G.-J, Shi F. Synlett 2016; 27: 2515
    • 2b Mei G.-J, Shi F. J. Org. Chem. 2017; 82: 7695
    • 2c Yan J, Ji X, Hua S, Wang J. Chin. J. Org. Chem. 2018; 38: 791
    • 2d Zhang Y.-C, Jiang F, Shi F. Acc. Chem. Res. 2020; 53: 425
    • 2e Cerveri A, Bandini M. Chin. J. Chem. 2020; 38: 287
    • 2f Tan B. Chin. J. Org. Chem. 2020; 40: 1404
  • 3 For an early report: Rong Z.-Q, Wang M, Chow CH. E, Zhao Y. Chem. Eur. J. 2016; 22: 9483

    • For (4+1) annulation:
    • 4a Wang C.-S, Li T.-Z, Cheng Y.-C, Zhou J, Mei G.-J, Shi F. J. Org. Chem. 2019; 84: 3214
    • 4b Chen T, Zhang Y, Fu Z, Huang W. Asian J. Org. Chem. 2019; 8: 2175

      For (4+2) annulation:
    • 5a Gu Z, Wu B, Jiang G.-F, Zhou Y.-G. Chin. J. Chem. 2018; 36: 1130
    • 5b Fan T, Zhang Z.-J, Zhang Y.-C, Song J. Org. Lett. 2019; 21: 7897
    • 5c Li X, Yan J, Qin J, Lin S, Chen W, Zhan R, Huang H. J. Org. Chem. 2019; 84: 8035
    • 5d Xie H.-P, Sun L, Wu B, Zhou Y.-G. J. Org. Chem. 2019; 84: 15498
    • 5e Marques A.-S, Duhail T, Marrot J, Chataigner I, Coeffard V, Vincent G, Moreau X. Angew. Chem. Int. Ed. 2019; 58: 9969
    • 5f Qi J, Tang H, Chen C, Cui S, Xu G. Org. Chem. Front. 2019; 6: 2760
    • 5g Frankowski S, Skrzyńska A, Sieroń L, Albrecht Ł. Adv. Synth. Catal. 2020; DOI: in press; 10.1002/adsc.202000197.

      For (4+3) annulation:
    • 6a Chen J, Huang Y. Org. Lett. 2017; 19: 5609
    • 6b Gao Z.-H, Chen K.-Q, Zhang Y, Kong L.-M, Li Y, Ye S. J. Org. Chem. 2018; 83: 15225
    • 6c Chen J, Jia P, Huang Y. Org. Lett. 2018; 20: 6715
    • 6d Chen K.-Q, Gao Z.-H, Ye S. Org. Chem. Front. 2019; 6: 405
    • 6e Trost BM, Zuo Z. Angew. Chem. Int. Ed. 2020; 59: 1243
    • 6f Liu Y.-Z, Wang Z, Huang Z, Zheng X, Yang W.-L, Deng W.-P. Angew. Chem. Int. Ed. 2020; 59: 1238
    • 6g Kumari P, Liu W, Wang C.-J, Dai J, Wang M.-X, Yang Q.-Q, Deng Y.-H, Shao Z. Chin. J. Chem. 2020; 38: 151
  • 7 For (4+4) annulation: Ni H, Tang X, Zheng W, Yao W, Ullah N, Lu Y. Angew. Chem. Int. Ed. 2017; 56: 14222

    • For (4+5) annulation:
    • 8a Yang L.-C, Rong Z.-Q, Wang Y.-N, Tan ZY, Wang M, Zhao Y. Angew. Chem. Int. Ed. 2017; 56: 2927
    • 8b Rong Z.-Q, Yang L.-C, Liu S, Yu Z, Wang Y.-N, Tan ZY, Huang R.-Z, Lan Y, Zhao Y. J. Am. Chem. Soc. 2017; 139: 15304
  • 9 For (4+6) annulation: Wang Y.-N, Yang L.-C, Rong Z.-Q, Liu T.-L, Liu R, Zhao Y. Angew. Chem. Int. Ed. 2018; 57: 1596
  • 10 For other annulations: Zeng R, Shan C, Liu M, Jiang K, Ye Y, Liu T.-Y, Chen Y.-C. Org. Lett. 2019; 21: 2312

    • For 1,4-addition:
    • 11a Gu Z, Zhou J, Jiang G.-F, Zhou Y.-G. Org. Chem. Front 2018; 5: 1148
    • 11b Gu Z, Xie J.-J, Jiang G.-F, Zhou Y.-G. Asian J. Org. Chem. 2018; 7: 1561
    • 11c Lin W, Zhang C, Xu W, Cheng Y, Li P, Li W. Adv. Synth. Catal. 2019; 361: 476
    • 11d Lin W, Lin X, Cheng Y, Chang X, Zhou S, Li P, Li W. Org. Chem. Front. 2019; 6: 2452
    • 11e Xie H.-P, Wu B, Wang X.-W, Zhou Y.-G. Chin. J. Catal. 2019; 40: 1566
    • 11f Zhang C, Cheng Y, Li F, Luan Y, Li P, Li W. Adv. Synth. Catal. 2020; 362: 1286
    • 11g Wang C, Yang Q, Wang M, Shang Y, Tong X, Deng Y, Shao Z. Org. Chem. Front. 2020; 7: 609
    • 11h Hu D, Gao Y, Song X, Du W, Chen Y.-C. Eur. J. Org. Chem. 2020; 514
    • 11i Xie H.-P, Wu B, Chen M.-W, Yu C.-B, Li H.-W, Li X, Zhou Y.-G. Chin. J. Org. Chem. 2020; DOI: in press; 10.6023/cjoc202003005.

      For some examples:
    • 12a Kawada M, Watanabe M, Okamoto K, Sugihara H, Hirata T, Maki Y, Imada I, Sanno Y. Chem. Pharm. Bull. 1984; 32: 3532
    • 12b Youssefyeh RD, Campbell HF, Klein S, Airey JE, Darkes P, Powers M, Schnapper M, Neuenschwander K, Fitzpatrick LR. J. Med. Chem. 1992; 35: 895
    • 12c Braun M, Hessamian-Alinejad A, de Lacroix BF, Alvarez BH, Fischer G. Molecules 2008; 13: 995
    • 12d Larghi EL, Kaufman TS. ARKIVOC 2011; (vii): 49
    • 13a Zhang H.-H, Wang C.-S, Li C, Mei G.-J, Li Y, Shi F. Angew. Chem. Int. Ed. 2017; 56: 116
    • 13b Ma C, Jiang F, Sheng F.-T, Jiao Y, Mei G.-J, Shi F. Angew. Chem. Int. Ed. 2019; 58: 3014
    • 13c Wang C.-S, Li T.-Z, Liu S.-J, Zhang Y.-C, Deng S, Jiao Y, Shi F. Chin. J. Chem. 2020; 38: 543
    • 13d Sheng F.-T, Li Z.-M, Zhang Y.-Z, Sun L.-X, Zhang Y.-C, Tan W, Shi F. Chin. J. Chem. 2020; 38: 583

      For some reviews on p-QMs:
    • 14a Caruana L, Fochi M, Bernardi L. Molecules 2015; 20: 11733
    • 14b Parra A, Tortosa M. ChemCatChem 2015; 7: 1524
    • 14c Chauhan P, Kaya U, Enders D. Adv. Synth. Catal. 2017; 359: 888
    • 14d Li W, Xu X, Zhang P, Li P. Chem. Asian J. 2018; 13: 2350
    • 14e Lima CG. S, Pauli FP, Costa DC. S, de Souza AS, Forezi LS. M, Ferreira VF, da Silva FC. Eur. J. Org. Chem. 2020; 2650

      For catalytic asymmetric (4+1) annulations:
    • 15a Liu L, Yuan Z, Pan R, Zeng Y, Lin A, Yao H, Huang Y. Org. Chem. Front. 2018; 5: 623
    • 15b Zielke K, Kovac O, Winter M, Pospisil J, Waser M. Chem. Eur. J. 2019; 25: 8163
    • 15c Lu H, Zhang H.-X, Tan C.-Y, Liu J.-Y, Wei H, Xu P.-F. J. Org. Chem. 2019; 84: 10292
    • 15d Tan J.-P, Yu P, Wu J.-H, Chen Y, Pan J, Jiang C, Ren X, Zhang H.-S, Wang T. Org. Lett. 2019; 21: 7298

      For catalytic asymmetric (4+2) annulations:
    • 16a Zhao K, Zhi Y, Shu T, Valkonen A, Rissanen K, Enders D. Angew. Chem. Int. Ed. 2016; 55: 12104
    • 16b Zhang L, Liu YK, Liu Z, He N, Li W. Org. Biomol. Chem. 2017; 15: 8743
    • 16c Zhang L, Zhou X, Li P, Liu Z, Liu Y, Sun Y, Li W. RSC Adv. 2017; 7: 39216
    • 16d Zhang Z.-P, Xie K.-X, Yang C, Li M, Li X. J. Org. Chem. 2018; 83: 364
    • 16e Jiang X.-L, Wu S.-F, Wang J.-R, Mei G.-J, Shi F. Adv. Synth. Catal. 2018; 360: 4225
    • 16f Yang G.-H, Zhao Q, Zhang Z.-P, Zheng H.-L, Chen L, Li X. J. Org. Chem. 2019; 84: 7883
    • 16g Tan J.-P, Zhang H, Jiang Z, Chen Y, Ren X, Jiang C, Wang T. Adv. Synth. Catal. 2020; 362: 1058
    • 16h Zhao M.-X, Xiang J, Zhao Z.-Q, Zhao X.-L, Shi M. Org. Biomol. Chem. 2020; 18: 1637

    • For racemic (4+2) annulations:
    • 16i Mei G.-J, Xu S.-L, Zheng W.-Q, Bian C.-Y, Shi F. J. Org. Chem. 2018; 83: 1414
    • 16j Zhou J.-Y, Ma C, Zhang Y.-Z, Wu Q, Shi F. Org. Biomol. Chem. 2018; 16: 9382
    • 16k Cao Z, Zhou G.-X, Ma C, Jiang K, Mei G.-J. Synthesis 2018; 50: 1307
    • 16l Yuan F.-R, Jiang F, Chen K.-W, Mei G.-J, Wu Q, Shi F. Org. Biomol. Chem. 2019; 17: 2361

      For catalytic asymmetric (4+3) annulations:
    • 17a Li W, Yuan H, Liu Z, Zhang Z, Cheng Y, Li P. Adv. Synth. Catal. 2018; 360: 2460
    • 17b Liu Q, Li S, Chen X.-Y, Rissanen K, Enders D. Org. Lett. 2018; 20: 3622
    • 17c Jiang F, Yuan F.-R, Jin L.-W, Mei G.-J, Shi F. ACS Catal. 2018; 8: 10234
    • 17d Sun M, Ma C, Zhou S.-J, Lou S.-F, Xiao J, Jiao Y, Shi F. Angew. Chem. Int. Ed. 2019; 58: 8703
    • 17e Liu L, Zhang J. Chin. J. Org. Chem. 2019; 39: 3308

      For reviews:
    • 18a Harmata M. Chem. Commun. 2010; 46: 8904
    • 18b Harmata M. Chem. Commun. 2010; 46: 8886
    • 18c Lohse AG, Hsung RP. Chem. Eur. J. 2011; 17: 3812
    • 18d Lam H, Lautens M. Synthesis 2020; DOI: in press; 10.1055/s-0039-1690875.
        1919
      • 19a CCDC 2007585 contains 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.
      • 19b See the Supporting Information for details.