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RESEARCH PRODUCT

Indoloquinolines, Indolobenzoxazines and Quinazolophthalazines Prepared from Norbornane/eneamino Acids and Hydrazides

Angela E. SzabóGéza StájerReijo SillanpääGyörgy TúrósPál Sohár

subject

chemistry.chemical_compoundchemistryOrganic ChemistryX-ray crystallographyOrganic chemistryNuclear magnetic resonance spectroscopyMother liquorPhysical and Theoretical ChemistryNorbornaneBlock (periodic table)Medicinal chemistry

description

The reactions of di-endo- and di-exo-aminonorbornane/enecarboxylic acids 1–4 with ethyl 2-(2-oxocyclohexyl)acetate afforded methanoindoloquinolines 5, 6, 8, and 9, the oxo ester participating as a two-membered sp2 building block. In the cases of di-exo- and di-endo-aminonorbornenecarboxylic acids 2 and 4, methanoindolobenzoxazinediones 7 and 10 were also formed; compound 7 was also isolated from the mother liquor of 10. The reactions of ethyl 2-(2-oxocyclohexyl)acetate with aminonorbornane/enecarbohydrazides 11–14 result in the methanoquinazolophthalazines 15–18. The structures of the compounds were elucidated by NMR spectroscopy, and for 6, 7, 8, and 10 also by X-ray crystallography. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

yearjournalcountryeditionlanguage
2005-08-18European Journal of Organic Chemistry
https://doi.org/10.1002/ejoc.200500155