Synlett 2012; 23(12): 1755-1758
DOI: 10.1055/s-0031-1289787
letter
© Georg Thieme Verlag Stuttgart · New York

Regioselective, Catalyst-Free, One-Step Synthesis of ABCD-Fused Hetero­cyclic Ring System, Closely Related to Circumdatin Alkaloids

Muhammad Yaqub*
a  Department of Chemistry, Bahauddin Zakariya University, Multan, Pakistan
,
Ruqayia Perveen
a  Department of Chemistry, Bahauddin Zakariya University, Multan, Pakistan
,
Zahid Shafiq
a  Department of Chemistry, Bahauddin Zakariya University, Multan, Pakistan
,
Humayun Pervez
a  Department of Chemistry, Bahauddin Zakariya University, Multan, Pakistan
,
Muhammad Nawaz Tahir
b  Department of Physics, University of Sargodha, Sargodha, Pakistan, Fax: +92(61)9210138   Email: mayaqub2@yahoo.com
› Author Affiliations
Further Information

Publication History

Received: 23 March 2012

Accepted after revision: 11 May 2012

Publication Date:
14 June 2012 (online)


Abstract

A novel method for the synthesis of tetracyclic fused-ring heterocycles, closely related to circumdatin alkaloids, is developed via regioselective reaction of heterocyclic ketene aminals (HKA) with 3-formylchromones.

Supporting Information

 
  • References and Notes

  • 1 Kumar K, Waldmann H. Angew. Chem. Int. Ed. 2009; 48: 3224
    • 2a Yaqub M, Yu C.-Y, Jia Y.-M, Huang Z.-T. Synlett 2008; 1357
    • 2b Xu W.-Y, Jia Y.-M, Yang J.-K, Huang Z.-T, Yu C.-Y. Synlett 2011; 1682
    • 3a Rahbaek L, Breinholt J. J. Nat. Prod. 1999; 62: 904
    • 3b Ookura R, Kito K, Ooi T, Namikoshi M, Kusumi T. J. Org. Chem. 2008; 73: 4245
    • 3c Lopez-Gresa MP, Gonzalez MC, Primo J, Moya P, Romero V, Estornell E. J. Antibiot. 2005; 58: 416
    • 3d Dai J.-R, Carte BK, Sidebottom PJ, Yew AL. S, Ng SW, Huang Y, Butler MS. J. Nat. Prod. 2001; 64: 125
    • 3e Raebaek L, Breinholt J. J. Nat. Prod. 1999; 62: 904
    • 3f Raebaek L, Breinholt J, Frisvald JC, Christopherson C. J. Org. Chem. 1999; 64: 1689
    • 3g Zhang D, Yang X, Kang JS, Choi HD, Son BW. J. Antibiot. 2008; 61: 40
    • 3h Bock MG, DiPardo RM, Rittle KE, Evans BE, Freidinger RM, Veber DF, Chang RS. L, Chen TB, Keegan ME, Lotti VJ. J. Med. Chem. 1986; 29: 1941
    • 3i Lopez-Gresa MP, Gonzalez MC, Primo J, Moya P, Romero V, Estornell E. J. Antibiot. 2005; 58: 416
    • 3j Sun HH, Barrow CJ, Sedlock DM, Gillum AM, Cooper R. J. Antibiot. 1994; 47: 515
    • 4a Li M, Zhou Z.-M, Wen L.-R, Qiu Z.-X. J. Org. Chem. 2011; 76: 3054
    • 4b Yan S.-J, Chen Y.-L, Liu L, Tang Y.-J, Lin J. Tetrahedron Lett. 2011; 52: 465
    • 4c Ungoren SK, Koca I, Yilmaz F. Tetrahedron 2011; 67: 5409
    • 4d Wen L.-R, Jiang C.-Y, Li M, Wang L.-J. Tetrahedron 2011; 67: 293
    • 4e Yu F, Yan S, Hu L, Wang Y, Lin J. Org. Lett. 2011; 13: 4782
    • 4f Wen LR, Liu C, Li M, Wang L.-J. J. Org. Chem. 2010; 75: 7605
    • 4g Yan S, Huang C, Su C, Ni Y, Lin J. J. Comb. Chem. 2010; 12: 91
    • 4h Yang L.-J, Yan S.-J, Chen W, Lin J. Synthesis 2010; 3536
    • 5a For reviews, see: Huang Z.-T, Wang M.-X. Heterocycles 1994; 37: 1233
    • 5b Liu B, Wang M.-X, Huang Z.-T. Tetrahedron Lett. 1999; 40: 7399
    • 5c Wang L.-B, Huang Z.-T. Synth. Commun. 1997; 27: 409
    • 5d Huang Z.-T, Yang J.-K. Heteroat. Chem. 1992; 3: 487
    • 5e Huang Z.-T, Wang X.-J. Tetrahedron Lett. 1987; 28: 1527
    • 5f Zhang J.-H, Wang M.-X, Huang Z.-T. J. Chem. Soc., Perkin Trans. 1 1999; 321
    • 6a Chen X.-M, Li Z.-J, Huang Z.-T. Carbohydr. Res. 2000; 328: 253
    • 6b Chen X.-M, Li Z.-J, Ren Z.-X, Huang Z.-T. Carbohydr. Res. 1999; 315: 262
    • 6c Yu C.-Y, Yang P.-H, Zhao M.-X, Huang Z.-T. Synlett 2006; 1835
    • 6d Hammouda M, Abou Zeid ZM, Metwally MA. Chem. Heterocycl. Compd. 2005; 41: 1525
    • 7a Zhang J.-H, Wang M.-X, Huang Z.-T. J. Chem. Soc., Perkin Trans. 1 1999; 2087
    • 7b Wang M.-X, Miao W.-S, Cheng Y, Huang Z.-T. Tetrahedron 1999; 55: 14611
    • 7c Nie X.-P, Wang M.-X, Huang Z.-T. Synthesis 2000; 1439
    • 8a Huang Z.-T, Liu Z.-R. Synth. Commun. 1989; 19: 1801
    • 8b Zhao M.-X, Wang Z.-M, Wang M.-X, Yan C.-H, Huang Z.-T. Tetrahedron 2002; 58: 7791
    • 8c Yu C.-Y, Wang L.-B, Li W.-Y, Huang Z.-T. Synthesis 1996; 959
    • 8d Liao J.-P, Zhang T, Yu C.-Y, Huang Z.-T. Synlett 2007; 761
    • 9a Plaskon AS, Grygorenko OO, Ryabukhin SV. Tetrahedron 2012; 68: 2743
    • 9b Baskar B, Dakas P.-Y, Kumar K. Org. Lett. 2011; 13: 1988
    • 9c Siddiqui ZN, Musthafa TN. M. Tetrahedron Lett. 2011; 52: 4008
    • 9d Naskar S, Banerjee M, Hazra A, Mondal S, Maity A, Paira R, Sahu KB, Saha P, Banerjee S, Mondal NB. Tetrahedron Lett. 2011; 52: 1527
    • 9e Lacova M, Gasparova R, Kois P, Bohac A, El-Shaaer HM. Tetrahedron 2010; 66: 1410
    • 9f Lacova M, Gasparova R, Loos D, Liptay T, Pronayova N. Molecules 2000; 5: 167
    • 9g Maiti S, Panja SK, Bandyopadhyay C. J. Heterocycl. Chem. 2010; 47: 973
    • 9h Plaskon AS, Ryabukhin SV, Volochnyuk DM, Gavrilenko KS, Shivanyuk AN, Tolmachev AA. J. Org. Chem. 2008; 73: 6010
    • 10a Diwakar SD, Joshi RS, Gill CH. J. Heterocycl. Chem. 2011; 48: 882
    • 10b Verspohl EJ, Bozdag-Dundar O, Kaup RM, Bauer K, Ertan R. Med. Chem. Res. 2009; 18: 665
    • 10c Ali TE, Abdel-Aziz SA, El-Shaaer HM, Hanafy FI, El-Fauomy AZ. Phosphorus, Sulfur Silicon Relat. Elem. 2008; 183: 2139
    • 10d Bozdag-Dundar O, Evranos B, Das-Evcimen N, Sarıkaya M, Ertan R. Eur. J. Med. Chem. 2008; 2412
    • 10e Panja SK, Karmakar P, Chakraborty J, Ghosh T, Bandyopadhyay C. Tetrahedron Lett. 2008; 49: 4397
    • 10f Plaskon AS, Ryabukhin SV, Volochnyuk DM, Shivanyuk AN, Tolmachev AA. Tetrahedron 2008; 64: 5933
    • 10g Karale BK, Chavan VP, Mane AS, Hangarge RV, Gill CH, Shingare MS. Synth. Commun. 2002; 32: 497
  • 11 General Procedure for the Synthesis of Compounds 7c, 8a–e, 9b–e, 10b–e, 11b,d, 12b,d The ketene aminals 4, 5, and 6 (1.29 mmol) were mixed separately with 3-formylchromones 2 and 3 (1.29 mmol) in CH2Cl2 (40 mL) and stirred at r.t. for 30 min. The reaction mixtures were then heated under reflux for 1–3.5 h. The solvent was removed under reduced pressure, and the residue was crystallized in EtOAc to afford the target compound 7c, 8ae, 9be, 10be, 11b,d, 12b,d. Representative Data of Heterocycle 8a Yellow solid; mp 238–240 °C. IR (KBr): 3475, 3352, 1655, 1626, 1555, 1499, 1469, 1418, 1356, 1333, 1303, 1251, 1209, 1163, 887, 746, 707, 622, 551 cm–1. 1H NMR (400 MHz, DMSO-d 6): δ = 2.26 (s, 3 H, CH3), 3.88 (s, 4 H, CH2CH2), 6.34 (s, 1 H, C11′-H), 6.93 (d, J = 8.4 Hz, 1 H, C10-H), 7.34–7.52 (m, 8 H, C5-H, C7-H, C9-H, and Ph-H), 9.46 (s, 1 H, NH). 13CNMR (100 MHz, DMSO-d 6): δ = 20.11 (CH3), 43.29 (CH2), 45.53 (CH2), 85.32 (CH), 91.06, 108.17, 117.71 (CH), 123.46, 126.42 (CH), 127.45 (CH), 128.28 (CH), 129.80 (CH), 131.25, 135.84 (CH), 135.93 (CH), 140.14, 153.75, 158.71, 178.45, 189.16. MS (EI): m/z (relative intensity, %): 358 (100) [M+], 343 (5), 329 (80), 301 (17), 253 (36), 225 (33), 195 (13), 179 (7), 135 (6), 105 (17), 77 (25). Anal. Calcd (%) for C22H18N2O3: C, 73.73; H, 5.06; N, 7.82. Found: C, 73.68; H, 5.03; N, 7.80
  • 12 The crystal structure of 8d has been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 865838