High yielding microwave-assisted synthesis of 2-(arylmethyl)amino-4-arylamino-6-alkyl-1,3,5-triazines

Tetrahedron Letters

Volumn 51, Issue 24, 2010, Pages 3174-3176

  Chen, Huixiong ^a   Dao, Pascal ^a   Laporte, Alice ^a   Garbay, Christiane ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

2 (Arylmethyl)amino 4 arylamino 6 alkyl 1,3,5 triazines; Cyclocondensation; Microwave synthesis

Indexed keywords

ALKYL GROUP; AMINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TRIAZINE DERIVATIVE;

ARTICLE; CYCLIZATION; MICROWAVE IRRADIATION; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; SYNTHESIS;

EID: 77953123627     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.04.042     Document Type: Article

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20. All MV reactions were performed in a BenchMate monomode reactor (IR detector for temperature) from CEM corporation.General procedure: A mixture of dicyandiamide (10.8 mmol, 1 equiv), arylamine (10.8 mmol, 1 equiv), and concentrated HCl (10.8 mmol, 1 equiv) in dioxane (20 ml) was introduced into a 50 mL round-bottomed flask equipped with a condenser and a magnetic stirring bar. The flask was placed in the microwave cavity and subjected to microwave irradiation for 15 min at 90 °C using irradiation power of 150 W. After cooling to room temperature, the arylbiguanide hydrochloride salt was precipitated. The solid was collected by filtration, washed with dioxane.
21. 6) δ: 2.18 (3H, s), 3.61 (3H, s), 3.75 (6H, s), 6.92 (2H, s, br), 7.20 (2H, s), 9.29 (1H, s). MS (ESI) m/z 292.1 (M+1).
22. 2) to afford the desired product as a white solid.
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24. 6) δ: 3.63 (3H, s), 3.77 (6H, s), 7.17 (2H, s), 7.88 (2H, s, br), 10.04 (1H, s). MS (ESI) m/z 346.1 (M+1).
25. 6) δ: 3.62 (3H, s), 3.76 (6H, s), 7.12 (2H, s), 7.16 (2H, s), 8.14 (1H, s), 9.36 (1H, s). MS (ESI) m/z 278.1 (M+1).
26. 6) δ: 2.14 (3H, s), 3.64 (3H, s), 3.68 (6H, s), 5.29 (2H, s), 6.55 (2H, s), 6.92 (2H, s), 7.60 (1H, t, J = 8 Hz), 7.75 (1H, d, J = 8 Hz), 8.15 (2H, m). MS (ESI) m/z 427.1 (M+1).
27. 6) δ: 2.13 (3H, s), 3.65 (3H, s), 3.67 (6H, s), 5.16 (2H, s), 6.50 (2H, s), 6.89 (2H, s), 7.29 (2H, s), 7.45 (2H, s). MS (ESI) m/z 460.1 (M+1).
28. 6) δ: 2.11 (3H, s), 3.63 (3H, s), 3.67 (6H, s), 5.24 (2H, s), 6.62 (2H, s), 6.88 (2H, s), 7.31 (2H, s), 7.43 (2H, s). MS (ESI) m/z 416.1 (M+1).
29. 6) δ: 2.12 (3H, s), 2.25 (3H, s), 3.64 (9H, s), 5.12 (2H, s), 6.48 (2H, s), 6.84 (2H, s), 7.10 (4H, m). MS (ESI) m/z 396.1 (M+1).
30. 2) to give the desired product.