Diazabicycloalkanes with nitrogen atoms in bridgehead positions 20. Synthesis of naphtho[2,3-b]-1,4-diazabicyclo[2.2.2]octene
- 58 Downloads
Reaction of 2-acetamido-3-bis(2-hydroxyethyl)aminonaphthalene with phosphorus oxychloride leads to the formation of 2-methyl-1-(2-chloroethyl)naphtho[2,3-d]imidazole, while reaction with hydrobromic acid gives naphtho[23-b]-1,4-diozabicyclo[2.2.2]octane in 13% yield. The yield of the latter can be increased to 45% by exchange of the hydroxyl groups in the starting material by chlorine and by deacetylation.
KeywordsNitrogen Phosphorus Hydroxyl Organic Chemistry Chlorine
Unable to display preview. Download preview PDF.
- 1.N. P. Luk'yanchuk, V. N. Sil'nikov, and G. V. Shishkin,Khim. Geterotsikl. Soedin., No. 8, 1106 (1989).Google Scholar
- 2.G. V. Shishkin and G. A. Zloba, USSR Author's Certificate No. 749,835;Byull. Izobret., No. 27, 101 (1980).Google Scholar
- 3.G. V. Shishkin and A. A. Gall',Khim. Geterotsikl. Soedin., No. 6, 827 (1980).Google Scholar
- 4.G. A. Shishkin and A. A. Gall',Khim. Geterotsikl. Soedin., No. 6, 831 (1980).Google Scholar
- 5.G. V. Shishkin,Khim. Geterotsikl. Soedin., No. 10, 1407 (1984).Google Scholar
- 6.Yu. Kirchne,Thin Layer Chromatography [Russian translation], Mir, Moscow (1981), Vol. 1, p. 463.Google Scholar
- 7.F. Sachs,Ber.,39, 3022 (1906).Google Scholar