Preparation of novel pyridine-fused tris-heterocycles; pyrido[4,3-e]pyrrolo-/pyrido[4,3-e]furano[2,3-c]pyridazines and pyrido[3,4-b]pyrrolo[3,2-d]pyrrole |
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Authors: | Vegar Stockmann |
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Affiliation: | Department of Chemistry, Norwegian University of Science and Technology, NTNU, N-7491 Trondheim, Norway |
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Abstract: | Three novel pyrido-fused tris-heterocycles have been prepared based on a Suzuki coupling and subsequent cyclisation approach. Pyrido[4,3-e]pyrrolo[2,3-c]pyridazine (3b, 77%) and pyrido[4,3-e]furano[2,3-c]pyridazine (5b, 76%) were obtained by intramolecular diazocoupling. Successful diazocoupling of furan (5b) is thus reported for the first time by NOBF4 generation of the diazonium intermediate. N-TIPS-pyrido[3,4-b]pyrrolo[3,2-d]pyrrole (TIPS-4b) was synthesised by thermal cyclisation of pyridyl nitrene in considerably higher yield (71%) than previously experienced from similar cyclisations, due to TIPS-activation. |
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Keywords: | Pyrido[4,3-e]pyrrolo[2,3-c]pyridazine Pyrido[4,3-e]furano[2,3-c]pyridazine, N-TIPS-pyrido[3,4-b]pyrrolo[3,2-d]pyrrole Diazotisation Diazocoupling Azide thermal decomposition 4-(3-Furanyl)pyridin-3-amine 4-(3-Pyrrolyl)pyridin-3-amine |
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