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Volumn 76, Issue 2, 2008, Pages 1007-1010

Facile and efficient synthesis of 1,4-benzodiazepines from 1,4-naphthoquinones

Author keywords

1,4 Naphthoquinone; 1,5 Benzodiazepine; Cyclization; Potassium Carbonate; Triethylamine

Indexed keywords

EID: 61349187761 PISSN: 03855414 EISSN: None Source Type: Journal
DOI: 10.3987/COM-08-S(N)63 Document Type: Article

Times cited : (13)

References (9)

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- Tandon V.K., Maurya H.K., Yadav D.B., Tripathi A., Kumar M., and Shukla P.K. Bioorg. Med. Chem. Lett. 16 (2006) 5883
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- Ryu, C.K.¹ Shim, J.Y.² Chae, M.J.³ Choi, I.H.⁴ Han, J.Y.⁵ Jung, O.J.⁶ Lee, J.Y.⁷ Jeong, S.H.⁸

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9
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- General procedure (3 and 4, To a solution of 2,3-dichloro-1,4-napthoquinone 1 (1 g, 4.40 mmol) in abs. EtOH (100 mL, 2-aminobenzonitrile 2 (0.52 g, 4.40 mmol) was added followed by anhydrous K2CO3 (435 mg, 4.40 mmol, The reaction mixture was vigorously stirred at 50 °C for 24 h. The reaction mixture was distilled and dried in vacuo. The mixture of 3 and 4 was separated by column chromatography (SiO2) using EtOAc in hexane (0-35, General Procedure (6, To a solution of 2-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2yl)aminobenzonitrile 3 (308 mg, 1 mmol) in abs. EtOH (90 mL, isopropylamine (71 mg, 1.2 mmol) and triethylamine (121 mg, 1.2 mmol) were added. The mixture was stirred first at rt for 0.5 h and then at 80-90 °C for 10-38 h. The reaction mixture was distilled and dried in vacuo and purified by flash column chromatography (SiO2) using EtOAc in hexane 0-15
- 2) using EtOAc in hexane (0-15%).

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