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Synthesis and reactions of pyrido[3,2,1-jk]carbazole-4,6-diones

✍ Scribed by Wolfgang Stadlbauer; Hoai Van Dang; Bernd Knobloch

Publisher
Journal of Heterocyclic Chemistry
Year
2011
Tongue
English
Weight
200 KB
Volume
48
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Pyrido[3,2,1‐jk]carbazoles 1, synthesized from carbazoles and alkyl‐ or arylmalonates, gave regioselective electrophilic substitution reactions at position 5 such as chlorination to 5‐chloro derivatives 2, nitration to 5‐nitro compounds 3, or hydroxylation to 5‐hydroxy derivatives 4. 5‐Hydroxy compounds 4 gave on treatment with strong bases ring contraction to 5, 6 or the ring opening product 7. Exchange of the chloro group in 2 with azide or amines gave the corresponding azides 8 and the 5‐amino derivatives 9 and 10. Alkylation of 1 with benzyl chloride or allyl bromide resulted in the formation of 5‐C‐alkylated products 11 together with 4‐alkyloxy derivatives 12. J. Heterocyclic Chem., 48, 1039 (2011).

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## Abstract magnified image Amination of 4‐hydroxypyridocarbazolones **1** with aniline or benzylamine gave in good yields 4‐amines **3**. With piperidine in a sealed tube from 4‐hydroxy‐ or 4‐chloro‐5‐alkylpyridocarbazolones **1** or **4** ring opened 1‐acylcarbazoles **5** were obtained. Only 4‐