- Activation of 6-bromoquinoline by nitration: Synthesis of morpholinyl and piperazinyl quinolones
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Quinoline forms the key skeletal component of a number of important natural products and pharmacologically-Active compounds. Despite a tremendous amount of research pertaining to the derivatization of quinoline, very few general synthetic routes are described in the literature starting from quinoline or tetrahydroquinoline. A simple and convenient method for the polyfunctionalization of quinolines via nitration of bromoquinolines has been developed. This method represents a new synthetic approach to convert brominated nitroquinoline derivatives into useful cyclic amines via nucleophilic-substitution (SNAr) reaction. Formula parented.
- ?akmak, Osman,?kten, Salih,Alimli, Dilek,Saddiqa, Aisha,Ersanli, Cem C?neyt
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- A Mild and General Larock Indolization Protocol for the Preparation of Unnatural Tryptophans
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A mild and general protocol for the Pd(0)-catalyzed heteroannulation of o-bromoanilines and alkynes is described. Application of a Pd(0)/P(tBu)3 catalyst system enables the efficient coupling of o-bromoanilines at 60 °C, mitigating deleterious side reactions and enabling access to a broad range of useful unnatural tryptophans. The utility of this new protocol is demonstrated in the highly convergent total synthesis of the bisindole natural product (-)-aspergilazine A.
- Chuang, Kangway V.,Kieffer, Madeleine E.,Reisman, Sarah E.
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p. 4750 - 4753
(2016/09/28)
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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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