- Synthesis of fused systems in the isoquinoline series: Oxazolo- and pyrrolo[3,2-c]isoquinolines
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In order to synthesize the pyrrolo[3,2-c]isoquinoline structure, three different routes starting from readily available isoquinolines were tried. The ring closure reaction of a malonic derivative of 4-amino-3- bromoisoquinoline led to an oxazolo[3,2-c]isoquinoline instead of the target molecule. This latter was obtained via Sonagashira coupling reaction followed by ring closure under basic conditions. A study of the lithiation of the N- sulfonated pyrrolo[3,2-c]isoquinoline was undertaken. After optimization of the lithiation conditions, various 2-substituted pyrrolo[3,2-c]isoquinolines were obtained and their oxidation reactions studied.
- Briere, Jean-Francois,Dupas, Georges,Queguiner, Guy,Bourguignon, Jean
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p. 1371 - 1383
(2007/10/03)
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- PHOTOLYSIS OF PYRIDYL, QUINOLYL, AND ISOQUINOLYL AZIDES IN HYDROHALOGENOIC ACIDS
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Photolysis of 4-azido-pyridine and -quinoline in hydrohalogenoic acids gave the 3-amino-4-halogeno compounds (2) via azirine or azacycloheptatetraene intermediates, whereas their N-oxides (4), under similar conditions, gave the 4-amino-3-halogeno compounds (5) presumably via nitrenium ion intermediates.In the 3-azidoquinoline and 4-azidoisoquinoline series, both free bases (6a, 8a) and N-oxides (6b, 8b) gave similar results to 4-azidopyridine and -quinoline N-oxides (4).
- Sawanishi, Hiroyuki,Hirai, Toyoko,Tsuchiya, Takashi
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p. 1043 - 1046
(2007/10/02)
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