Selectivities in the formation of pyridines and pyrimidines by ammonia-induced cyclocondensations of vinamidiniums

Balasubrahmanyam, S. N.; Bommuswamy, Jeyashri; Namboothiri, Irishi N. N.

doi:10.1016/s0040-4020(01)85295-9

Cited by 19 publications

(14 citation statements)

References 21 publications

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“…White solid, 103 mg (GC yield 46%, Isolated yield 45%). 1 H NMR, 13 C NMR data were consistent with the published data. 1 2,6-Di(4-fluorophenyl)pyridine (3b).…”

Section: 6-diphenylpyridine (3a)supporting

confidence: 88%

“…1 H NMR, 13 C NMR data were consistent with the published data. 1 2,6-Di(4-fluorophenyl)pyridine (3b). Brown solid, 115 mg (Isolated yield 43%, GC yield 47%).…”

Section: 6-diphenylpyridine (3a)supporting

confidence: 88%

“…Colorless liquid, 222 mg (GC yield 70%, Isolated yield 52%) 1 H NMR (CDCl 3 , Me 4 Si) δ 1.00 (t, J = 7.3 Hz, 6H), 1.64 (q, J = 7.6 Hz, 4H), 2.04-2.13 (m, 2H), 2.55 (t, J = 7.8 Hz, 4H), 2.90 (t, J = 7.4 Hz, 4H), 6.95 (s, 2H); 13…”

Section: 7-di-n-propyl-23-dihydroindene (2d)mentioning

confidence: 99%

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Unprecedented Double C—C Bond Cleavage of a Cyclopentadienyl Ligand.

Sato

et al. 2003

ChemInform

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Reactions of organo-metal compounds Reactions of organo-metal compounds O 0350Unprecedented Double C-C Bond Cleavage of a Cyclopentadienyl Ligand. -An unprecedented cleavage of the cyclopentadienyl ring of titanacyclopentadienes (III), (VIII), and (XI), which are generated in situ, by treatment with nitriles is reported.By chemical experiments, a mechanism is proposed involving the cleavage of one cyclopentadienyl ligand and transformation of the resulting pieces such as a two-carbon unit and a three-carbon unit into a benzene derivative and a pyridine derivative. -(XI*, Z.; SATO, K.; GAO, Y.; LU, J.; TAKAHASHI, T.; J. Am. Chem. Soc. 125 (2003) 32, 9568-9569; Dep. Chem., Peking Univ.,

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“…White solid, 103 mg (GC yield 46%, Isolated yield 45%). 1 H NMR, 13 C NMR data were consistent with the published data. 1 2,6-Di(4-fluorophenyl)pyridine (3b).…”

Section: 6-diphenylpyridine (3a)supporting

confidence: 88%

“…1 H NMR, 13 C NMR data were consistent with the published data. 1 2,6-Di(4-fluorophenyl)pyridine (3b). Brown solid, 115 mg (Isolated yield 43%, GC yield 47%).…”

Section: 6-diphenylpyridine (3a)supporting

confidence: 88%

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Unprecedented Double C—C Bond Cleavage of a Cyclopentadienyl Ligand.

Sato

et al. 2003

ChemInform

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“…Similarly, the reaction of 36 with p-bromoanisol in the presence of the same catalyst leads to 3,5-di(p-anisyl)pyridine (45) [21] in 67% yield. These results indicate that the reactivity of the bis(tri-n-butylstannylated)aromatic compounds is similar to that founded in other Stille reactions carried out with trimethylstannyl susbstituted aromatic systems [22].…”

Section: Methodsmentioning

confidence: 98%

Sonochemical synthesis of bis(tri-n-butylstannyl) aromatic compounds via Barbier-like reactions

Gerbino

Fidelibus

Mandolesi

et al. 2013

Journal of Organometallic Chemistry

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“…The products, after conventional workup, were purified by flash chromatography on silica gel, eluting with n ‐hexane/ethyl acetate mixtures. Products are all known and were identified by comparison of physical and spectroscopic data with those given in the cited references: 3a ,60 3b and 3c ,61 3d ,62 3e ,63 3f ,64 3g ,65 3h ,66 3i ,67 and 3j . [68]…”

Section: Methodsmentioning

confidence: 99%

A Mild and Versatile Method for Palladium‐Catalyzed Cross‐Coupling of Aryl Halides in Water and Surfactants

et al. 2003

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Various aqueous surfactants proved to be excellent media for carrying out palladium-catalyzed Suzuki−Miyaura cross-coupling reactions under mild conditions. The dehalogenation side reaction, which is usually a drawback with the aqueous protocol, was not observed. The concentration of the surfactant in water played a pivotal role for the reaction outcome. Smooth cross-coupling of iodoanisole and a variety of aryl bromides, including electron-rich derivatives, with aryl boronic acids occurred at room temperature in high yields either with [Pd(PPh3)4] or Pd/C as catalyst. The water-surfactant Pd/C system combines high activity under ambient conditions (air), easy separation and recyclability. Palladium acetate was found to be effective in cross-coupling of the less reactive aryl chlorides at 100 °C

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Selectivities in the formation of pyridines and pyrimidines by ammonia-induced cyclocondensations of vinamidiniums

Cited by 19 publications

References 21 publications

Unprecedented Double C—C Bond Cleavage of a Cyclopentadienyl Ligand.

Unprecedented Double C—C Bond Cleavage of a Cyclopentadienyl Ligand.

Sonochemical synthesis of bis(tri-n-butylstannyl) aromatic compounds via Barbier-like reactions

A Mild and Versatile Method for Palladium‐Catalyzed Cross‐Coupling of Aryl Halides in Water and Surfactants

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