Ring closure reaction of 5-hydroxy-pyrido[2,3-d]pyrimidine-2,4,7-triones to benzo[b]pyrimido[4,5-h]1,6-naphthyridine-1,3,6-triones

N-Substituted aminouracils (1) react with malonates by cyclocondensation to 5-hydroxy-pyrido [2,3-d] pyrimidine-2,4,7-triones (2), which give with triethylorthoformate and aniline 6-(phenylaminomethylene)-pyrido[2,3-d]pyrimidine-tetraone (3). Halogenation of 2a-d (with R(2) = Me) with phosphorylchlo...

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Published inJournal für praktische Chemie, Chemiker-Zeitung Vol. 338; no. 2; pp. 151 - 156
Main Authors Khattab, AFA, VanTinh, D, Stadlbauer, W
Format Journal Article
LanguageEnglish
Published HEIDELBERG JOHANN AMBROSIUS BARTH VERLAG 01.01.1996
Subjects
Chemistry
Chemistry, Applied
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
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Summary:N-Substituted aminouracils (1) react with malonates by cyclocondensation to 5-hydroxy-pyrido [2,3-d] pyrimidine-2,4,7-triones (2), which give with triethylorthoformate and aniline 6-(phenylaminomethylene)-pyrido[2,3-d]pyrimidine-tetraone (3). Halogenation of 2a-d (with R(2) = Me) with phosphorylchloride leads to 5,7-dichloro-pyrido [2,3-d]pyrimidine-2,4-diones (4) by cleavage of the methyl group at N-8, whereas Vilsmeier reaction of 2 affords 5-chloro-6-formyl derivatives (6), which cyclize with arylamines to give benzo[b]pyrimido[4,5-h] 1,6-naphthyridines (9). Compounds 9 were obtained independently by amination of the tosylates 5 to the 5-arylamino compounds 8, and Vilsmeier formylation to yield 9.
ISSN:0941-1216
DOI:10.1002/prac.19963380129