1983
DOI: 10.1021/jo00153a014
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Base-catalyzed rearrangement of N-(aryloxy)pyridinium salts. Effect of a 3-substituent in the pyridine ring upon orientation. Synthesis of novel tricyclic rings

Abstract: The orientation in the base-catalyzed rearrangement of 3-substituted jV-(aryloxy)pyridinium tetrafluoroborates (5) to 2or 6-(2-hydroxyaryl)pyridines has been studied. A 3-methyl group directs exclusively to the 6-position while inductively electron-withdrawing substituents (Cl, Br, I, OMe, C02Me, COMe) direct mainly, if not exclusively, to C-2. The phenols derived from 3-C02Me derivatives cyclize spontaneously to the substituted pyrido[3,2djcoumarins (8) in useful yields, and that from the 3-COMe compound give… Show more

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Cited by 16 publications
(18 citation statements)
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“…While surveying the literature, it was found that the first synthesised pyridocoumarin derivatives was reported by Rudolph A. Abramovitch by the construction of pyran ring (Figure d) and prior to 2000 there were only limited reports on the synthesis and biological evaluation of polynuclear azaarene fused coumarin derivatives. However, after a few years post 2000, a number of syntheses of such derivatives have been reported by various groups of scientists indicating the gradual increase in the interest on the synthesis and biological evaluation of such compounds.…”
Section: Different Technique For the Synthesis Of Pyridocoumarin Derimentioning
confidence: 99%
“…While surveying the literature, it was found that the first synthesised pyridocoumarin derivatives was reported by Rudolph A. Abramovitch by the construction of pyran ring (Figure d) and prior to 2000 there were only limited reports on the synthesis and biological evaluation of polynuclear azaarene fused coumarin derivatives. However, after a few years post 2000, a number of syntheses of such derivatives have been reported by various groups of scientists indicating the gradual increase in the interest on the synthesis and biological evaluation of such compounds.…”
Section: Different Technique For the Synthesis Of Pyridocoumarin Derimentioning
confidence: 99%
“…The following S-and O-allyl compounds were prepared by treatment of the appropriate aryl 2-mercaptobenzoate or aryl 2hydroxybenzoate with allyl bromide in DMF in the presence of potassium carbonate as previously described. 25 Typical products are reported here, the remainder are described in the ESI †: (18) and 108 (26).…”
Section: Aryl 2-(allyloxy)benzoates 5 and Aryl 2-(allylthio)benzoatesmentioning
confidence: 99%
“…The addition of ether (6 cm 3 ) completed the crystallisation of the products (0.74 g, 72%). The picrate of the minor isomer 32 was partially purified by recrystallisation (0.26 g, 25%), mp 204-207 • C (from nitromethane) (lit., 18…”
Section: Fvp Of Phenyl 2-(allyloxy)benzoate 5amentioning
confidence: 99%
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“…The advent of palladium chemistry has exerted a profound impact on the synthesis of heterocycles. 1 During the course of our research, we investigated the utility of palladium chemistry in the synthesis of benzo [4,5]furopyridines. These heterocycles often display important biological activities 2 and are also useful biosteres for dibenzofuran.…”
mentioning
confidence: 99%