Synthesis 2019; 51(12): 2523-2531
DOI: 10.1055/s-0037-1611525
special topic
© Georg Thieme Verlag Stuttgart · New York

Ruthenium(II)-Catalyzed Migratory C–H Allylation/Hydroamination Cascade for the Synthesis of Rutaecarpine Analogues

Gurupada Bairy
a   Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, West Bengal, India   Email: rjana@iicb.res.in
b   Academy of Scientific and Innovative Research (AcSIR), Jadavpur, Kolkata 700032, West Bengal, India
,
Arijit Nandi
a   Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, West Bengal, India   Email: rjana@iicb.res.in
,
Kartic Manna
a   Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, West Bengal, India   Email: rjana@iicb.res.in
b   Academy of Scientific and Innovative Research (AcSIR), Jadavpur, Kolkata 700032, West Bengal, India
,
Ranjan Jana*
a   Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, West Bengal, India   Email: rjana@iicb.res.in
b   Academy of Scientific and Innovative Research (AcSIR), Jadavpur, Kolkata 700032, West Bengal, India
› Author Affiliations
This work was financially supported by the Department of Science and Technology (DST), Science and Engineering Research Board (SERB), Government of India (Ramanujan Fellowship Award No. SR/S2/RJN-97/2012, Extra Mural Research Grant No. EMR/2014/000469). G.B. thanks UGC and K.M. thanks CSIR for their fellowships.
Further Information

Publication History

Received: 11 March 2019

Accepted after revision: 27 March 2019

Publication Date:
26 April 2019 (online)


Published as part of the Special Topic Ruthenium in Organic Synthesis

Abstract

An unprecedented allyl migration from a remote position of a quinazoline moiety through a ruthenium(II) shuttle is reported. This present cascade reaction is initiated through the formation of an η3-ruthenium–allyl complex followed by C–H allylation at the ortho position of the 2-aryl moiety. Finally, hydroamination with the quinazolinone -NH group, which is formed through tautomerization of the quinazoline, furnishes the annulation product. This exceedingly fast cascade reaction is complete within 10 minutes to provide rutaecarpine analogues in a single operation.

Supporting Information

 
  • References

    • 1a Lechat P, Tesleff S, Bownan WC. Aminopyridines and Similarly Acting Drugs . Pergamon; Oxford: 1982
    • 1b Vacher B, Bonnaud B, Funes P, Jubault N, Koek W, Assie MB, Cosi C. J. Med. Chem. 1998; 41: 5070
    • 1c Andersohn F, Konzen C, Garbe E. Ann. Intern. Med. 2007; 146: 657
    • 1d Martarelli D, Pompei P, Baldi C, Mazzoni G. Cancer Chemother. Pharmacol. 2008; 61: 809
    • 1e Fang J, Ji H, Lawton GR, Xue F, Roman LJ, Silverman RB. J. Med. Chem. 2009; 52: 4533
    • 1f Hilton S, Naud S, Caldwell J, Boxall K, Burns S, Anderson VE, Antoni L, Allen CE, Pearl LH, Oliver AW, Ahern GW, Garrett MD, Collins I. Bioorg. Med. Chem. 2010; 18: 707
    • 2a Grover GS, Kini G. Eur. J. Med. Chem. 2006; 41: 256
    • 2b Jatav V, Kashaw S, Mishra P. Med. Chem. Res. 2008; 17: 205
    • 2c Rohini R, Reddy PM, Shanker K, Hu A, Ravinder V. Eur. J. Med. Chem. 2010; 45: 1200
    • 2d Shallcross LJ, Davies SC. J. Antimicrob. Chemother. 2014; 69: 2883
    • 2e Jafari E, Khajouei MR, Hassanzadeh F, Hakimelahi GH, Khodarahmi GA. Res. Pharm. Sci. 2016; 11: 1
    • 3a Kadi AA, El-Azab AS, Alafeefy AM, Abdel-Hamide SG. Al-Azhar J. Pharm. Sci. 2006; 34: 147
    • 3b Giri RS, Thaker HM, Giordano T, Williams J, Rogers D. Eur. J. Med. Chem. 2009; 44: 2184
    • 3c Wang D, Gao F. Chem. Cent. J. 2013; 7: 95
    • 3d Bouley R, Kumarasiri M, Peng Z, Otero LH, Song W. J. Am. Chem. Soc. 2015; 137: 1738
    • 3e Jafari E, Khajouei MR, Hassanzadeh F, Hakimelahi GH, Khodarahmi GA. Res. Pharm. Sci. 2016; 11: 1
    • 3f Lv Z, Wang B, Hu Z, Zhou Y, Yu W, Chang J. J. Org. Chem. 2016; 81: 9924
    • 3g Shinde AH, Arepally S, Baravkar MD, Sharada DS. J. Org. Chem. 2017; 82: 331
    • 3h Yao S, Zhou K, Wang J, Cao H, Yu L, Wu J, Qiu P, Xu Q. Green Chem. 2017; 19: 2945
    • 4a Shen C, Wang L, Wen M, Shen H, Jin J, Zhang P. Ind. Eng. Chem. Res. 2016; 55: 3177
    • 4b Zhang Q, Li Y, Zhang B, Lu B, Li J. ‎Bioorg. Med. Chem. Lett. 2017; 27: 4885

      For selected reviews on C–H activation, see:
    • 5a Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
    • 5b He J, Wasa M, Chan KS. L, Shao Q, Yu J.-Q. Chem. Rev. 2017; 117: 8754
    • 5c Xue X.-S, Ji P, Zhou B, Cheng J.-P. Chem. Rev. 2017; 117: 8622
    • 5d Yang Y, Lan J, You J. Chem. Rev. 2017; 117: 8787
    • 5e Newton CG, Wang S.-G, Oliveira CC, Cramer N. Chem. Rev. 2017; 117: 8908
    • 5f Kim D.-S, Park W.-J, Jun C.-H. Chem. Rev. 2017; 117: 897
    • 5g Yi H, Zhang G, Wang H, Huang Z, Wang J, Singh AK, Lei A. Chem. Rev. 2017; 117: 9016
    • 5h Shang R, Ilies L, Nakamura E. Chem. Rev. 2017; 117: 9086
    • 5i Hummel JR, Boerth JA, Ellman JA. Chem. Rev. 2017; 117: 9163
    • 6a Duncton MA. J. MedChemComm 2011; 2: 1135
    • 6b Caro-Diaz EJ. E, Urbano M, Buzard DJ, Jones RM. Bioorg. Med. Chem. Lett. 2016; 26: 5378
    • 7a Manna MK, Hossian A, Jana R. Org. Lett. 2015; 17: 672
    • 7b Manna MK, Bhunia SK, Jana R. Chem. Commun. 2017; 53: 6906
    • 7c Manna MK, Bairy G, Jana R. J. Org. Chem. 2018; 83: 8390
    • 7d Bairy G, Das S, Begam HM, Jana R. Org. Lett. 2018; 20: 7107

      For reviews on the Fujiwara–Moritani Heck reaction, see:
    • 8a Le Bras J, Muzart J. Chem. Rev. 2011; 111: 1170
    • 8b Zhou L, Lu W. Chem. Eur. J. 2014; 20: 634

    • For seminal work, see:
    • 8c Moritani I, Fujiwara Y. Tetrahedron Lett. 1967; 8: 1119
  • 9 Zheng Y, Song W.-B, Zhang S.-W, Xuan L.-J. Org. Biomol. Chem. 2015; 13: 6474
    • 10a Manikandan R, Jeganmohan M. Org. Lett. 2014; 16: 3568
    • 10b Wu J, Xiang S, Zeng J, Leow M, Liu X.-W. Org. Lett. 2015; 17: 222
    • 10c Bian J, Qian X, Wang N, Mu T, Li X, Sun H, Zhang L, You Q, Zhang X. Org. Lett. 2015; 17: 3410
    • 11a Cui S, Zhang Y, Wu Q. Chem. Sci. 2013; 4: 3421
    • 11b Cui S, Zhang Y, Wang D, Wu Q. Chem. Sci. 2013; 4: 3912
    • 11c Wu S, Zeng R, Fu C, Yu Y, Zhang X, Ma S. Chem. Sci. 2015; 6: 2275
  • 12 Lou M, Deng Z, Mao X, Fu Y, Yang Q, Peng Y. Org. Biomol. Chem. 2018; 16: 1851
  • 13 Xia Y.-Q, Dong L. Org. Lett. 2017; 19: 2258
  • 14 Feng Y, Tian N, Li Y, Jia C, Li X, Wang L, Cui X. Org. Lett. 2017; 19: 1658
    • 15a Bhattacharyya J, Pakrashi SC. Heterocycles 1980; 14: 1469
    • 15b El-Soll AM. A. Global J. Biotechnol. Biochem. 2011; 6: 31
  • 16 Palem JD, Alugubelli GR, Bantu R, Nagarapu L, Polepalli S, Jain SN, Bathini R, Manga V. Bioorg. Med. Chem. Lett. 2016; 26: 3014
  • 17 Vemula SR, Kumar D, Cook GR. ACS Catal. 2016; 6: 5295
  • 18 Manoharan R, Jeganmohan M. Chem. Commun. 2015; 51: 2929
    • 19a Huang L, Wang Q, Qi J, Wu X, Huang K, Jiang H. Chem. Sci. 2013; 4: 2665
    • 19b Wang H, Schroder N, Glorius F. Angew. Chem. Int. Ed. 2013; 52: 5386
    • 20a Manikandan R, Madasamy P, Jeganmohan M. ACS Catal. 2016; 6: 230
    • 20b Manikandan R, Tamizmani M, Jeganmohan M. Org. Lett. 2017; 19: 6678
    • 21a Kim NY, Cheon C.-H. Tetrahedron Lett. 2014; 55: 2340
    • 21b Cheng R, Guo T, Zhang-Negrerie D, Du Y, Zhao K. Synthesis 2013; 45: 2998
    • 21c Hour M.-J, Yang J.-S, Chen T.-L, Chen K.-T, Kuo S.-C, Chung J.-G, Lu C.-C, Chen C.-Y, Chuang Y.-H. Eur. J. Med. Chem. 2011; 46: 2709
    • 21d Mahiwal K, Kumar P, Narasimhan B. Med. Chem. Res. 2012; 21: 293
    • 22a Purandare AV, Gao A, Wan H, Somerville J, Burke C, Seachord C, Vaccaro W, Wityak J, Poss MA. Bioorg. Med. Chem. Lett. 2005; 15: 2669
    • 22b Gellibert F, Fouchet M.-H, Nguyen V.-L, Wang R, Krysa G, de Gouville A.-C, Huet S, Dodic N. Bioorg. Med. Chem. Lett. 2009; 19: 2277