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Synlett 2012; 23(12): 1755-1758
DOI: 10.1055/s-0031-1289787
DOI: 10.1055/s-0031-1289787
letter
Regioselective, Catalyst-Free, One-Step Synthesis of ABCD-Fused Heterocyclic Ring System, Closely Related to Circumdatin Alkaloids
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.
Key words
heterocyclic ketene aminal - 3-formyl chromone - domino reaction - circumdatin D - circumdatin ESupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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- 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, 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