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

Muhammad Yaqub; Ruqayia Perveen; Zahid Shafiq; Humayun Pervez; Muhammad Nawaz Tahir

doi:10.1055/s-0031-1289787

Synlett, Table of Contents

Synlett 2012; 23(12): 1755-1758
DOI: 10.1055/s-0031-1289787

letter

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

Authors

Muhammad Yaqub*

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan, Pakistan
Ruqayia Perveen

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan, Pakistan
Zahid Shafiq

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan, Pakistan
Humayun Pervez

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan, Pakistan
Muhammad Nawaz Tahir

^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, Fax: +92(61)9210138 Email: mayaqub2@yahoo.com

Abstract

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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.

Key words

heterocyclic ketene aminal - 3-formyl chromone - domino reaction - circumdatin D - circumdatin E

Full Text

References

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, 8a–e, 9b–e, 10b–e, 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, C_11′-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

Supplementary Material

Supporting Information (PDF)

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

Authors

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