18. Condensation products of phenols and ketones. Part VII. Molecular complexes formed by 2′-hydroxy-2 : 4 : 4 : 7 : 4′-pentamethylflavan

Baker, Wilson; Curtis, R. F.; Edwards, M. G.

doi:10.1039/jr9510000083

Cited by 17 publications

(4 citation statements)

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“…Pyridine 4 e was coupled with compound 7, [19] which should have a much higher reactivity at C-2 than 5. The only isolable product was identical with the one obtained in the above reaction.…”

Section: Resultsmentioning

confidence: 99%

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5,5″-Disubstituted 2,2′:6′,2″-Terpyridines through and for Metal-Mediated Cross-Coupling Chemistry

1999

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The 0.3 ± 5 g scale syntheses of the 2,2':6',2''-terpyridines 3, 6, 9, and 10 are described. The pyridine units are connected to one another by Pd-catalyzed crosscoupling reactions. This method allows the easy introduction of halogen, stannyl, and boronic ester functionalities at positions C-5 and C-5''; this results in a novel functionality pattern for terpyridines that considerably widens the applicability of this class of tridentate ligands for supra-and macromolecular applications. The feasibility of growth reactions with these novel terpyridines was demonstrated by the synthesis of compounds 12 a ± c.

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Section: Resultsmentioning

confidence: 99%

“…Compounds 1 b, [10] 2 a, [13] 4 a, [16] and 11 [24] were prepared according to the literature. For compounds 2 b and 7, see references [14] and [19]. All other compounds are new.…”

Section: Methodsmentioning

confidence: 99%

5,5″-Disubstituted 2,2′:6′,2″-Terpyridines through and for Metal-Mediated Cross-Coupling Chemistry

1999

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“…An 1,2-addition elimination reaction of this lithio derivative with 2-bromopyridine failed under various conditions as well as its reaction with pyridine which only gave poor yields (20%) of bipyridine 3 . Then two cross-coupling reactions under Suzuki's conditions between either 3,4-dimethoxy-2-iodopyridine 7 and 2-(tributyltin)pyridine 8 or 3,4-dimethoxy-2-(tributyltin)pyridine and 2-iodopyridine were tested; these attempts failed, and only traces of 3 could be obtained in the second cross-coupling.…”

Section: Resultsmentioning

confidence: 99%

First Synthesis of Caerulomycin C

et al. 1996

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“…The hydrochloride salt of 2-chloropyridine on treatment with NaI in acetonitrile (reflux, 24 h) led to 2-iodopyridine (75%) [19]. On refluxing 2-bromopyridine with aqueous HI for 6 h, a low yield of 2-iodopyridine (35%) was obtained [20].…”

Section: Resultsmentioning

confidence: 97%

Facile acidic hydrolysis and displacement reactions of 2‐chloro‐and 2,9‐dichloro‐1,10‐phenanthroline

Krapcho

Sparapani

2008

Journal of Heterocyclic Chem

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Treatment of 2‐chloro‐ or 2,9‐dichloro‐1,10‐phenanthroline with aqueous HBr or aqueous H2SO4 at 120°C yielded 1,10‐phenanthroline‐2(1H)‐one or 1,10‐dihydro‐1,10‐phenanthroline‐2,9‐dione, respectively. The hydrolysis of 2,9‐dichloro‐1,10‐phenanthroline with 37% aqueous HC1 led to the half hydrolyzed amide and the bis‐amide. Under comparable reactions conditions, using aqueous HBr, H2SO4 or HC1, 2‐chloropyridine was found to be hydrolytically stable. On the other hand, 2‐chloro‐ or 2,9‐dichloro‐1,10‐phenanthroline on heating with 57% aqueous HI afforded the HI salts of 2‐iodo‐ or 2,9‐diiodo‐1,10‐phenanthroline, which could be isolated. These salts on treatment with aqueous ammonium hydroxide led to good yields of 2‐iodo‐ and 2, 9‐diiodo‐1,10‐phenanthroline, respectively. Treatment of 2‐chloropyridine with 57% aqueous HI under similar reaction conditions led to 2‐iodopyridine in a 10% conversion.

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18. Condensation products of phenols and ketones. Part VII. Molecular complexes formed by 2′-hydroxy-2 : 4 : 4 : 7 : 4′-pentamethylflavan

Cited by 17 publications

References 0 publications

5,5″-Disubstituted 2,2′:6′,2″-Terpyridines through and for Metal-Mediated Cross-Coupling Chemistry

5,5″-Disubstituted 2,2′:6′,2″-Terpyridines through and for Metal-Mediated Cross-Coupling Chemistry

First Synthesis of Caerulomycin C

Facile acidic hydrolysis and displacement reactions of 2‐chloro‐and 2,9‐dichloro‐1,10‐phenanthroline

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