Synthesis 2019; 51(11): 2359-2370
DOI: 10.1055/s-0037-1610685
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Decarboxylative [4+2] Cycloaddition of Vinyl Benzoxazinanones with Cyclic N-Sulfimines: Stereoselective Synthesis­ of Benzosulfamidate-Fused Tetrahydroquinazolines

Dasom Mun
,
Eunjin Kim
,
Sung-Gon Kim*
Department of Chemistry, Kyonggi University, 154-42 Gwanggyosan-ro, Yeongtong-gu, Suwon 16227, Republic of Korea   Email: sgkim123@kyonggi.ac.kr
› Author Affiliations
This research was supported by the Nanomaterial Technology Development Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning (NRF-2012M3A7B4049645), and the Basic Science Research Program through the NRF funded by the Ministry of Education (NRF-2016R1D1A1A09916621).
Further Information

Publication History

Received: 21 November 2018

Accepted after revision: 28 December 2018

Publication Date:
20 February 2019 (eFirst)

Abstract

Methods for the catalytic synthesis of highly functionalized benzosulfamidate-fused tetrahydroquinazolines are presented. The decarboxylative [4+2] cycloaddition of vinyl benzoxazinanones with benzoxathiazine 2,2-dioxides catalyzed by Pd(PPh3)4 affords fused-tetrahydroquinazolines with high diastereoselectivities. Alternatively, catalytic asymmetric [4+2] cycloaddition employing a chiral palladium-containing phosphoramidite ligand provides optically enriched benzosulfamidate-fused tetrahydroquinazolines in good yields and with excellent diastereoselectivities and enantioselectivities.

Supporting Information

 
  • References

    • 1a Heterocycles in Natural Product Synthesis . Majumdar KC, Chattopadhyay SK. Wiley-VCH; Weinheim: 2011
    • 1b Baumann M, Baxendale IR, Ley SV, Nikbin N. Beilstein J. Org. Chem. 2011; 7: 442
    • 1c Baumann M, Baxendale IR. Beilstein J. Org. Chem. 2013; 9: 2265
  • 2 Verdel BM, Souverein PC, Egberts AC. G, Leufkens HG. M. Ann. Pharm. 2006; 40: 1040 ; and references cited therein
  • 3 Corbett JW, Ko SS, Rodgers JD, Gearhart LA, Magnus NA, Bacheler LT, Diamond S, Jeffrey S, Klabe RM, Cordova BC, Garber S, Logue K, Trainor GL, Anderson PS, Erickson-Viitanen SK. J. Med. Chem. 2000; 43: 2019
    • 4a Rasul A, Yu B, Zhong L, Khan M, Yang H, Ma T. Oncol. Rep. 2012; 27: 1481
    • 4b Kobayashi Y, Nakano Y, Kizaki M, Hoshikuma K, Yokoo Y, Kamiya T. Planta Med. 2001; 67: 628
    • 5a Cheng X, Vellalath S, Goddard R, List B. J. Am. Chem. Soc. 2008; 130: 15786
    • 5b Rueping M, Antonchick AP, Sugiono E, Grenader K. Angew. Chem. Int. Ed. 2009; 48: 908
    • 5c Prakash M, Kesavan V. Org. Lett. 2012; 14: 1896
    • 5d Cheng D.-J, Tian Y, Tian S.-K. Adv. Synth. Catal. 2012; 354: 995
    • 5e Prakash M, Jayakumar S, Kesavan V. Synthesis 2013; 45: 2265
    • 5f Huang D, Li X, Xu F, Li L, Lin X. ACS Catal. 2013; 3: 2244
    • 5g Armstrong RJ, D’Ascenzio M, Smith MD. Synlett 2016; 27: 6
    • 5h Sui Y, Cui P, Liu S, Zhou Y, Du P, Zhou H. Eur. J. Org. Chem. 2018; 215
    • 6a He Y.-P, Du Y.-L, Luo S.-W, Gong L.-Z. Tetrahedron Lett. 2011; 52: 7064
    • 6b He Y.-P, Wu H, Chen D.-F, Yu J, Gong L.-Z. Chem. Eur. J. 2013; 19: 5232
    • 6c Wang YN, Wang BC, Zhang MM, Gao XW, Li TR, Lu L.-Q, Xiao WJ. Org. Lett. 2017; 19: 4094
  • 7 Sim J.-T, Kim H, Kim S.-G. Tetrahedron Lett. 2016; 57: 5907
    • 8a Wang C, Tunge JA. J. Am. Chem. Soc. 2008; 130: 8118
    • 8b Li T.-R, Tan F, Lu L.-Q, Wei Y, Wang YN, Liu Y.-Y, Yang Q.-Q, Chen J.-R, Shi D.-Q, Xiao W.-J. Nat. Commun. 2014; 5: 5500
    • 8c Wei Y, Lu L.-Q, Li T.-R, Feng B, Wang Q, Xiao W.-J, Alper H. Angew. Chem. Int. Ed. 2016; 55: 2200
    • 8d Guo C, Fleige M, Janssen-Müller D, Daniliuc CG, Glorius F. J. Am. Chem. Soc. 2016; 138: 7840
    • 8e Leth LA, Glaus F, Meazza M, Fu L, Thøgersen KM, Bitsch EA, Jørgensen KA. Angew. Chem. Int. Ed. 2016; 55: 12272
    • 8f Mei G.-J, Bian C.-Y, Li G.-H, Xu S.-L, Zheng W.-Q, Shi F. Org. Lett. 2017; 19: 3219
    • 8g Guo C, Janssen-Müller D, Fleige M, Lerchen A, Daniliuc CG, Glorius F. J. Am. Chem. Soc. 2017; 139: 4443
  • 9 During the preparation of this manuscript, a palladium-catalyzed enantioselective [4+2] cycloaddition reaction of vinyl benzoxazinones with sulfamate-derived cyclic imines was reported, see: Wang C, Li Y, Wu Y, Wang Q, Shi W, Yuan C, Zhou L, Xiao Y, Guo H. Org. Lett. 2018; 20: 2880
    • 10a Winum J.-Y, Scozzafava A, Montero J.-L, Supuran CT. Med. Res. Rev. 2005; 25: 186
    • 10b Winum J.-Y, Scozzafava A, Montero J.-L, Supuran CT. Expert Opin. Ther. Pat. 2006; 16: 27
    • 10c Woo LW. L, Purohit A, Potter BV. L. Mol. Cell. Endocrinol. 2011; 340: 175
    • 10d Williams SJ. Expert Opin. Ther. Pat. 2013; 23: 79
    • 10e Bower JF, Rujirawanich J, Gallagher T. Org. Biomol. Chem. 2010; 8: 1505
    • 10f Baig RB. N, Nadagouda MN, Varma RS. Aldrichimica Acta 2015; 48: 71

      For selected examples, see:
    • 11a Parthasarathy K, Azcargorta AR, Cheng Y, Bolm C. Org. Lett. 2014; 16: 2538
    • 11b Zhang H.-X, Nie J, Cai H, Ma J.-A. Org. Lett. 2014; 16: 2542
    • 11c Jiang C, Lu Y, Hayashi T. Angew. Chem. Int. Ed. 2014; 53: 9936
    • 11d Jiang T, Wang Z, Xu M.-H. Org. Lett. 2015; 17: 528
    • 11e Gigant N, Drège E, Retailleau P, Joseph D. Chem. Eur. J. 2015; 21: 15544
    • 11f Lai B.-N, Qiu J.-F, Zhang H.-X, Nie J, Ma J.-A. Org. Lett. 2016; 18: 520
    • 11g De Munck L, Vila C, Muñoz MC, Pedro JR. Chem. Eur. J. 2016; 22: 17590
    • 11h Quan M, Tang L, Shen J, Yang G, Zhang W. Chem. Commun. 2017; 53: 609
    • 11i De Munck L, Monleón A, Vila C, Pedro JR. Adv. Synth. Catal. 2017; 359: 1582
    • 11j Wu Y, Yuan C, Wang C, Mao B, Jia H, Gao X, Liao J, Jiang F, Zhou L, Wang Q, Guo H. Org. Lett. 2017; 19: 6268
    • 11k Jin J.-H, Wang H, Yang Z.-T, Yang W.-L, Tang W, Deng W.-P. Org. Lett. 2018; 20: 104
    • 12a Kim H, Kim Y, Kim S.-G. J. Org. Chem. 2017; 82: 8179
    • 12b Lee SG, Kim S.-G. RSC Adv. 2017; 7: 34283

      For selected reviews on chiral phosphoramidite ligands, see:
    • 13a Teichert J, Feringa BL. Angew. Chem. Int. Ed. 2010; 49: 2486
    • 13b Fu W, Tang W. ACS Catal. 2016; 6: 4814