Synthesis of 6H-Indolo[2,3-b][1,6]naphthyridines and Related Compounds as the 5-Aza Analogues of Ellipticine Alkaloids

Autor:	Hai-Ren Zhang, Quan Zhang, Kung K. Wang, Chongsheng Shi
Rok vydání:	2000
Předmět:	Ellipticine Aza Compounds chemistry.chemical_compound chemistry Organic Chemistry Thermal decomposition Substituent Organic chemistry Antineoplastic Agents Ellipticines Naphthyridines
Zdroj:	The Journal of Organic Chemistry. 65:7977-7983
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo000978e
Popis:	Treatment of 2-(1-alkynyl)phenyl isocyanates 6 with the iminophosphorane 14 produced in situ the benzoenynyl carbodiimides 15. Thermolysis of 15 under refluxing p-xylene furnished the 6H-indolo[2,3-b][1,6]naphthyridines 5, which could be regarded as the 5-aza analogues of ellipticine alkaloids. Similarly, condensation of 6 with the iminophosphorane 20 led to the formation of the 6H-indolo[2,3-b][1,5]naphthyridines 25 as the major isomer and the 10H- indolo[2,3-b][1,7]naphthyridines 26 as the minor isomer. The indolonaphthyridines 32, 33, and 34 having a methoxyl substituent were likewise synthesized. Treatment of the diisocyanate 43 with 2 equiv of the iminophosphorane 7 furnished 45 having two indoloquinoline units incorporated in a seven-fused-ring system.
Databáze:	OpenAIRE
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