One-Step Synthesis of 1, 2, 3, 4-Tetrahydrobenzo[g]quinazoline-5, 10-dione Derivatives from Vitamin K3

Shunsaku OHTA; Yasunari HINATA; Masayuki YAMASHITA; Ikuo KAWASAKI; Yoko JINDA; Shinobu HORIE

doi:10.1248/cpb.42.1730

One-Step Synthesis of 1, 2, 3, 4-Tetrahydrobenzo[g]quinazoline-5, 10-dione Derivatives from Vitamin K₃

Shunsaku OHTA, Yasunari HINATA, Masayuki YAMASHITA, Ikuo KAWASAKI, Yoko JINDA, Shinobu HORIE

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Keywords: 2-methyl-1, 4-naphthoquinone, 1, 2, 3, 4-tetrahydrobenzo[g]quinazoline, formaldehyde, amination, quinonemethide, photochemical oxidation

JOURNAL FREE ACCESS

1994 Volume 42 Issue 9 Pages 1730-1735

DOI https://doi.org/10.1248/cpb.42.1730

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Abstract

The reactions of 2-halogenonaphthoquinones (5, 13, 14 and 15) and 2-methyl-1, 4-naphthoquinone (20; vitamin K₃) with primary and secondary amines were examined. 1, 3-Dialkyl-1, 2, 3, 4-tetrahydrobenzo[g]quinazoline-5, 10-diones (9) were obtained in moderate yields by treating 20 with formaldehyde in primary amines. A plausible reaction path-way is also presented.

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