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Copper catalysed synthesis of indolylquinazolinone alkaloid bouchardatine

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Abstract

We describe the total synthesis of indolylquinazolinone alkaloid bouchardatine and some of the quinazolinone derivatives. The aerobic oxidation induced by copper(I) bromide, followed by Vilsmeier-Haack formylation gives the natural product bouchardatine alkaloid in good yield.

2,3-Dihydroquinazolin-4(1H)-ones are an important class of privileged compounds which have a range of applications in many areas of chemistry and frequently found in many natural products. The aerobic oxidation induced by copper(I) bromide, followed by Vilsmeier-Haack formylation gives the natural product bouchardatine alkaloid in good yield.

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References

  1. (a) Mhaske S B and Argade N P 2006 Tetrahedron 62 9787; (b) Grundon M F 1984 Nat. Prod. Rep. 1 195; (c) Michael J P 2000 Nat. Prod. Rep. 17 603

  2. (a) Witt A and Bergman J 2003 Curr. Org. Chem. 7 659; (b) Johne S Rodd’s 1995 Chemistry of Carbon Compounds (supplements to the 2nd Ed.) (ed) Ansell M F (Amsterdam: Elsevier) Vol. IV I/J, pp 223; (c) Brown D J 1996, Quinazolines. In The Chemistry of Heterocyclic Compounds, Volume 55, Quinazolines: Supplement 1 (New York: Wiley); (d) Connolly D J, Cusack D, O’Sullivan T P and Guiry P J 2005 Tetrahedron 61 10153; (e) Liang J L, Cha H C and Jahng Y 2011 Molecules 16 4861; (f) Nacro K, Zha C, Guzzo P R, Herr R J, Peace D and Friedrich T D 2007 Bioorg. Med. Chem. 15 4237

  3. Wattanapiromsakul C, Forster P I and Waterman P G 2003 Phytochemistry 64 609

  4. Richards PG 1991 Bouchardatia Vol. 2 Harden G, (Ed.), (Sydney: New South Wales University Press)

  5. Forster P I 2002 Rutaceae R J F Henderson (Ed.), (Brisbane: Queensland Government, Environmental Protection Agency)

  6. (a) Bubenyák M, Palfi M, Takacs M, Beni S, Eva S, Noszal B and Kokosi J 2008 Tetrahedron Lett. 49 4937; (b) Naik N H, Urmode T D, Sikder A K and Kusurkar R S 2013 Aust. J. Chem. 66 1112

  7. (a) Jana R, Pathak T P and Sigman M S 2011 Chem. Rev. 111 1417; (b) Engle K M, Mei T S, Wang X and Yu J Q 2011 Angew. Chem., Int. Ed. 50 1478; (c) Bras J L and Muzart J 2011 Chem. Rev. 111 1170; (d) Chen X, Wang H, Jin X, Feng J, Wang Y and Lu P 2011 Chem. Commun. 47 2628; (e) Luo Y, Pan X and Wu J 2011 Org. Lett. 13 1150; (f) Armstrong A and Collins J C 2010 Angew. Chem., Int. Ed. 49 2282; (g) Zhao D B, You J S and Hu C W 2011 Chem.- Eur. J. 17 5466

  8. For general reviews on palladium-catalyzed transformations and synthesis of heterocycles, see: (a) Magano J and Dunetz J R 2011 Chem. Rev. 111 2177; (b) Majumdar K C, Chattopadhyay B K, Maji P K, Chattopadhyay S and Samanta S 2010 Heterocycles 81 795; (c) Song G, Wang F and Li X 2012 Chem. Soc. Rev. 41 3651; (d) Neufeldt S R and Sanford M S 2012 Acc. Chem. Res. 45 936; (e) Kuhl N, Hopkinson M N, Wencel D J and Glorius F 2012 Angew. Chem., Int. Ed 51 10236; (f) Mousseau J J and Charette A B 2013 Acc. Chem. Res. 46 412

  9. For reviews and papers on copper-catalyzed coupling reactions, see: (a) Lanting X, Yinsheng P, Qiangbiao P, Yongwen J and Dawei M 2013 J. Org. Chem. 78 3400; (b) Allen S E, Walvoord R R, Salinas R P and Kozlowski M 2013 Chem. Rev. 113 6234; (c) Xiaolin P, Yong L and Jie W 2013 J. Org. Chem. 78 5756; (d) Chen D S, Dou G L, Li Y L, Liu Y and Wang X S 2013 J. Org. Chem. 78 5700; (e) Biswas S and Batra S 2013 Eur. J. Org. Chem. 4895; (f) Jhan Y H, Kang T W and Hsieh J C 2013 Tetrahedron Lett. 54 1155; (g) Chen D, Chen Q, Liu M, Dai S, Huang L, Yang J and Bao W 2013 Tetrahedron 69 6461; (h) Ngi S I, Guilloteau V, Abarbri M and Thibonnet J J 2011 Org. Chem. 76 8347; (i) Xu W, Jin Y, Liu H, Jiang Y and Fu H 2011 Org. Lett. 13 1274; (j) Sreenivas D K, Ramkumar N and Nagarajan R 2012 Org. Biomol. Chem. 10 3417

  10. (a) Salvatore R N, Nagle A S and Jung K W 2002 J. Org. Chem. 67 674; (b) Wolfe J P and Buchwald S L 2000 J. Org. Chem. 65 1144

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Acknowledgements

We thank the Department of Science and Technology (DST) (Project number: SR/S1/OC-70/2008) for financial support. M V thanks the Council of Scientific and Industrial Research (CSIR) for a Senior Research Fellowship.

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  1. School of Chemistry, University of Hyderabad, Hyderabad, 500 046, India

    MAYAVAN VIJI & RAJAGOPAL NAGARAJAN

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  1. MAYAVAN VIJI
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Correspondence to RAJAGOPAL NAGARAJAN.

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VIJI, M., NAGARAJAN, R. Copper catalysed synthesis of indolylquinazolinone alkaloid bouchardatine. J Chem Sci 126, 1075–1080 (2014). https://doi.org/10.1007/s12039-014-0637-5

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