Download PDF
Synthesis 2022; 54(10): 2423-2432
DOI: 10.1055/a-1731-2703
paper

N-Iodosuccinimide-Promoted Selective Construction of Cyclopropyl and Dihydrofuranyl Spirooxindoles from Alkylidene Oxindoles and Annular β-Dicarbonyl Compounds

Hong Chen
a   Anhui Province Key Laboratory of Functional Coordinated Complexes for Materials Chemistry Application, and School of Chemical and Environmental Engineering, Anhui Polytechnic University, Wuhu 241000, P. R. of China
,
Hui Xu∗
a   Anhui Province Key Laboratory of Functional Coordinated Complexes for Materials Chemistry Application, and School of Chemical and Environmental Engineering, Anhui Polytechnic University, Wuhu 241000, P. R. of China
,
Zeng-Yang He
b   Technology Center, China Tobacco Anhui Industrial Co., Ltd., 9 Tianda Road, Hefei 230088, P. R. of China
,
Peng Zou
b   Technology Center, China Tobacco Anhui Industrial Co., Ltd., 9 Tianda Road, Hefei 230088, P. R. of China
,
Fei-Hong Huang
a   Anhui Province Key Laboratory of Functional Coordinated Complexes for Materials Chemistry Application, and School of Chemical and Environmental Engineering, Anhui Polytechnic University, Wuhu 241000, P. R. of China
,
Ying Jin∗
a   Anhui Province Key Laboratory of Functional Coordinated Complexes for Materials Chemistry Application, and School of Chemical and Environmental Engineering, Anhui Polytechnic University, Wuhu 241000, P. R. of China
,
Ze Zhang∗
a   Anhui Province Key Laboratory of Functional Coordinated Complexes for Materials Chemistry Application, and School of Chemical and Environmental Engineering, Anhui Polytechnic University, Wuhu 241000, P. R. of China
› Author AffiliationsThis work was supported by the Natural Science Foundation of Anhui Province (2008085QB64), Foundation of Anhui Province Key Laboratory of Clean Energy Materials and Chemistry for Sustainable Conversion of Natural Resources (LCECSC-15), Pre-research Project of National Natural Science Foundation of Anhui Polytechnic University (Xjky2020079, 2019yyzr09), Foundation of China Tobacco Anhui Industrial Corporation (2020146) and Foundation of China National Tobacco Corporation (11201903003).
› Further Information
    Permissions and Reprints All articles of this category


Abstract

An efficient N-iodosuccinimide-promoted cyclization of readily available alkylidene oxindoles with annular β-dicarbonyl compounds has been demonstrated. With five-membered cyclic β-dicarbonyl compounds as the starting materials, a series of cyclopropyl oxindoles can be obtained in good to excellent yields, whereas the method affords dihydrofuranyl spirooxindoles almost quantitatively when six- or seven-membered cyclic β-dicarbonyl compounds are employed. This protocol provides a new alternative to the practical synthesis of structurally diverse spirooxindoles.

Key words

spirooxindoles - N-iodosuccinimide - β-dicarbonyl compounds - selective synthesis - cyclization

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1731-2703.
  • Supporting Information


Publication History

Received: 18 November 2021

Accepted after revision: 04 January 2022

Accepted Manuscript online:
04 January 2022

Article published online:
21 February 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Zheng Y, Tice CM, Singh SB. Bioorg. Med. Chem. Lett. 2014; 24: 3673
    CrossrefPubMed

      • For reviews on the synthesis of spirooxindoles, see:
    • 2a Hong L, Wang R. Adv. Synth. Catal. 2013; 355: 1023
      Crossref
    • 2b Cao Z.-Y, Zhou J. Org. Chem. Front. 2015; 2: 849
      Crossref
    • 2c Bariwal J, Voskressensky LG, Van der Eycken EV. Chem. Soc. Rev. 2018; 47: 3831
      CrossrefPubMed
    • 2d Boddy AJ, Bull JA. Org. Chem. Front. 2021; 8: 1026
      Crossref
    • 2e Saeed R, Sakla AP, Shankaraiah N. Org. Biomol. Chem. 2021; 19: 7768
      CrossrefPubMed
    • 3a Jiang T, Kuhen KL, Wolff K, Yin H, Bieza K, Caldwell J, Bursulaya B, Wu TY.-H, He Y. Bioorg. Med. Chem. Lett. 2006; 16: 2105
      CrossrefPubMed
    • 3b Jiang T, Kuhen KL, Wolff K, Yin H, Bieza K, Caldwell J, Bursulaya B, Tuntland T, Zhang K, Karanewsky D, He Y. Bioorg. Med. Chem. Lett. 2006; 16: 2109
      CrossrefPubMed
    • 3c He Y, Jiang T, Kuhen KL, Ellis Y.-H, Wu B, Wu TY.-H, Bursulaya B. WO 2004037247A1, 2004
      PubMed
    • 4a Sampson PB, Liu Y, Li S.-W, Forrest BT, Pauls HW, Edwards LG, Feher M, Patel NK. B, Laufer R, Pan G. WO 2010115279A1, 2010
      PubMed
    • 4b Chen L, Feng L, He Y, Huang M, Yun H. WO 2011070039A1, 2011
      PubMed
    • 4c Pauls HW, Li S.-W, Sampson PB, Forrest BT. WO 2012048411A1, 2012
      PubMed
    • 5a Deshpande AM, Barawkar D, Patil S, Bankar D. WO 2016088903A1, 2016
      PubMed
    • 5b Okano T, Suzuki S. JP 2015193573A, 2015
      PubMed
    • 6a Alper PB, Meyers C, Lerchner A, Siegel DR, Carreira EM. Angew. Chem. Int. Ed. 1999; 38: 3186
      CrossrefPubMed
    • 6b Wood JL, Holubec AA, Stoltz BM, Weiss MM, Dixon JA, Doan BD, Shamji MF, Chen JM, Heffron TP. J. Am. Chem. Soc. 1999; 121: 6326
      Crossref
    • 6c Marti C, Carreira EM. J. Am. Chem. Soc. 2005; 127: 11505
      CrossrefPubMed
    • 6d Helan V, Mills A, Drewry D, Grant D. J. Org. Chem. 2010; 75: 6693
      CrossrefPubMed
    • 7a Chowdhury S, Chafeev M, Liu S, Sun J, Raina V, Chui R, Young W, Kwan R, Fu J, Cadieux JA. Bioorg. Med. Chem. Lett. 2011; 21: 3676
      CrossrefPubMed
    • 7b Gupta N, Bhojani G, Tak R, Jakhar A, Khan NH, Chatterjee S, Kureshy RI. ChemistrySelect 2017; 2: 10902
      Crossref
    • 7c Hu W, Teng S, Shi T, Wei Y. CN 105710031A, 2016
      PubMed

      For selected examples on the synthesis of cyclopropyl spirooxindoles, see:
    • 8a Cao Z.-Y, Wang X, Tan C, Zhao X.-L, Zhou J, Ding K. J. Am. Chem. Soc. 2013; 135: 8197
      CrossrefPubMed
    • 8b Awata A, Arai T. Synlett 2013; 24: 29
    • 8c Noole A, Malkkov AV, Kanger T. Synthesis 2013; 45: 2520
      Article in Thieme Connect
    • 8d Zhang Z, Zhang Y, Huang G, Zhang G. Org. Chem. Front. 2017; 4: 1372
      Crossref
    • 8e Kuang Y, Shen B, Dai L, Yao Q, Liu X, Lin L, Feng X. Chem. Sci. 2018; 9: 688
      CrossrefPubMed
    • 8f Hajra S, Roy S, Saleh SA. Org. Lett. 2018; 20: 4540
      CrossrefPubMed
    • 8g Wang L, Cao W, Mei H, Hu L, Feng X. Adv. Synth. Catal. 2018; 360: 4089
      Crossref
    • 8h Song Y.-X, Du D.-M. Org. Biomol. Chem. 2019; 17: 5375
      CrossrefPubMed
    • 8i Chen L, He J. J. Org. Chem. 2020; 85: 5203
      CrossrefPubMed
    • 8j Zhang R.-Y, Jin F, Bao X.-G, Li H.-Y, Xu X.-P, Ji S.-J. J. Org. Chem. 2021; 86: 1141
      CrossrefPubMed
    • 8k Pramanik S, Ray S, Maity S, Ghosh P, Mukhopadhyay C. Synthesis 2021; 53: 2240
      Article in Thieme Connect

      For selected examples on the synthesis of dihydrofuranyl spirooxindoles, see:
    • 9a Liu Y.-L, Wang X, Zhao Y.-L, Zhu F, Zeng X.-P, Chen L, Wang C.-H, Zhao X.-L, Zhou J. Angew. Chem. Int. Ed. 2013; 52: 13735
      CrossrefPubMed
    • 9b Zhou R, Zhang K, Chen Y, Meng Q, Liu Y, Li R, He Z. Chem. Commun. 2015; 51: 14663
      CrossrefPubMed
    • 9c Kumarswamyreddy N, Kesavan V. Eur. J. Org. Chem. 2016; 5301
      Crossref
    • 9d Miao Y.-H, Hua Y.-Z, Wang M.-C. Org. Biomol. Chem. 2019; 17: 7172
      CrossrefPubMed
    • 9e Pan L.-N, Sun J, Shi R.-G, Yan C.-G. Org. Chem. Front. 2020; 7: 3202
      Crossref

      For selected examples, see:
    • 10a Li Y, Xu H, Xing M, Huang F, Jia J, Gao J. Org. Lett. 2015; 17: 3690
      CrossrefPubMed
    • 10b Wang J.-Y, Zhou P, Li G, Hao W.-J, Tu S.-J, Jiang B. Org. Lett. 2017; 19: 6682
      CrossrefPubMed
    • 10c Cao X, Cheng X, Xuan J. Org. Lett. 2018; 20: 449
      CrossrefPubMed
    • 10d Kathuria D, Gupta P, Chourasiya SS, Sahoo SC, Beifuss U, Chakraborti AK, Bharatam PV. Org. Biomol. Chem. 2019; 17: 4129
      CrossrefPubMed
    • 10e Xu H, Yu F, Huang R, Weng M, Chen H, Zhang Z. Org. Chem. Front. 2020; 7: 3368
      Crossref
    • 10f Feng J, He T, Xie Y, Yu Y, Baell JB, Huang F. Org. Biomol. Chem. 2020; 18: 9483
      CrossrefPubMed
    • 10g He L, Yang Y, Liu X, Liang G, Li C, Wang D, Pan W. Synthesis 2020; 52: 459
      Article in Thieme Connect
    • 10h Li X, Zheng L, Gong X, Chang H, Gao W, Wei W. J. Org. Chem. 2021; 86: 1096
      CrossrefPubMed
    • 10i Yu X.-X, Zhao P, Zhou Y, Huang C, Wang L.-S, Wu Y.-D, Wu A.-X. J. Org. Chem. 2021; 86: 12141
      CrossrefPubMed
    • 10j Xu C, Yin G, Jia F.-C, Wu Y.-D, Wu A.-X. Org. Lett. 2021; 23: 2559
      CrossrefPubMed
    • 11a Xu H, Liu H.-W, Lin H.-S, Wang G.-W. Chem. Commun. 2017; 53: 12477
      CrossrefPubMed
    • 11b Xu H, Hong R, Weng M.-Y, Huang R.-L, Wang G.-W, Zhang Z. Org. Lett. 2021; 23: 5305
      CrossrefPubMed
  • 12 Fang Q.-Y, Yi M.-H, Wu X.-X, Zhao L.-M. Org. Lett. 2020; 22: 5266
    CrossrefPubMed
    • 13a Xu H, Chen K, Liu H.-W, Wang G.-W. Org. Chem. Front. 2018; 5: 2864
      Crossref
    • 13b Xu H, Huang R.-L, Shu Z, Hong R, Zhang Z. Org. Biomol. Chem. 2021; 19: 4978
      CrossrefPubMed

      For selected examples, see:
    • 14a Gao W.-C, Hu F, Huo Y.-M, Chang H.-H, Li X, Wei W.-L. Org. Lett. 2015; 17: 3914
    • 14b Fan Y, He Y, Liu X, Hu T, Ma H, Yang X, Luo X, Huang G. J. Org. Chem. 2016; 81: 6820
      CrossrefPubMed
    • 14c Usami K, Nagasawa Y, Yamaguchi E, Tada N, Itoh A. Org. Lett. 2016; 18: 8
      CrossrefPubMed
    • 14d Guo Y.-J, Lu S, Tian L.-L, Huang E.-L, Hao X.-Q, Zhu X, Shao T, Song M.-P. J. Org. Chem. 2018; 83: 338
      CrossrefPubMed
    • 14e Xia B, Chen W, Zhao Q, Yu W, Chang J. Org. Lett. 2019; 21: 2583
      CrossrefPubMed
    • 14f Fang B, Hou J, Tian J, Yu W, Chang J. Org. Biomol. Chem. 2020; 18: 3312
      CrossrefPubMed
    • 14g Alizadeh A, Bagherinejad A, Khanpour M. Synthesis 2021; 53: 4059
      Article in Thieme Connect
  • 15 CCDC 2109675 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/structures
  • 16 Penjarla TR, Kundarapu M, Rangan K, Bhattacharya A. Org. Biomol. Chem. 2020; 18: 9623
    CrossrefPubMed
    • 17a Noole A, Sucman NS, Kabeshov MA, Kanger T, Macaev FZ, Malkov AV. Chem. Eur. J. 2012; 18: 14929
      CrossrefPubMed
    • 17b Tang C.-K, Zhou Z.-Y, Xia A.-B, Bai L, Liu J, Xu D.-Q, Xu Z.-Y. Org. Lett. 2018; 20: 5840
      CrossrefPubMed
    • 18a Banik BK, Fernandez M, Alvarez C. Tetrahedron Lett. 2005; 46: 2479
      Crossref
    • 18b Yin G, Fan L, Ren T, Zheng C, Tao Q, Wu A, She N. Org. Biomol. Chem. 2012; 10: 8877
      CrossrefPubMed
    • 18c Ahmed N, Babu BV. Synth. Commun. 2013; 43: 3044
      Crossref
    • 18d von der Heiden D, Bozkus S, Klussmann M, Breugst M. J. Org. Chem. 2017; 82: 4037
      CrossrefPubMed
    • 18e Takeda Y, Kajihara R, Kobayashi N, Noguchi K, Saito A. Org. Lett. 2017; 19: 6744
      CrossrefPubMed
  • 19 Cao S.-H, Zhang X.-C, Wei Y, Shi M. Eur. J. Org. Chem. 2011; 2668
    Crossref