Synthesis of Cytisine Structural Analogs by Mannich Condensation of 5,7-Dinitro-8-hydroxyquinoline Anionic Adduct

Yakunina, I. E.; Shakhkel'dyan, I. V.; Atroshchenko, Yu. M.; Rybakova, A.S.; Troitskii, N. A.; Shuvalova, E. V.

doi:10.1007/s11178-005-0327-3

Cited by 9 publications

(6 citation statements)

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“…The same group also demonstrated that similar reactions could be performed using Grignard reagents in place of NaBH 4 . This methodology has since been extended to a variety of other m -dinitroaromatic, dinitrobicycloaromatic, and dinitroheteroaromatic rings. − …”

Section: Early Developmentsmentioning

confidence: 94%

Nitro-Mannich Reaction

2013

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Section: Early Developmentsmentioning

confidence: 94%

Nitro-Mannich Reaction

2013

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“…Quenching the reaction with orthophosphoric acid in place of acetic acid affords a slight increase of the yield of 557a . When the same sequence of reactions is carried out on 5,7-dinitro-8-hydroxyquinoline 943 , the expected 3-ABN derivatives 945 , which are analogues of 561 (see Schemes 80 and ) are obtained in moderate yield . A more interesting result is the dearomatization of 1-(2-hydroxyethoxy)-2,4-dinitrobenzene 946 through reduction with sodium borohydride (Scheme ).…”

Section: Note Added In Proofmentioning

confidence: 99%

Nucleophilic Dearomatizing (D_NAr) Reactions of Aromatic C,H-Systems. A Mature Paradigm in Organic Synthesis

et al. 2007

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Institute fu ¨r Kohlenforschung (Mu ¨lheim a.d. Ruhr) with R. Benn investigating 187 Os NMR. In November 1989 he became Profesor Titular at the University of Oviedo, where he started his own research. He moved to the University of Almerı ´a (1996), where he is Professor of Organic Chemistry. His current research activities range from the application of phosphorus-stabilized carbanions in organic and organometallic chemistry to mechanistic studies of reactions involving organometallic species through multinuclear magnetic resonance. G. Ruiz Go ´mez was born in Madrid, Spain. She studied chemistry at the University of Almerı ´a and completed her first degree (Licenciatura) in July 2000. She was awarded a Ph.D. in 2006 for work on dearomatizing reactions of phosphinamides and phosphonamides under the direction of Professor Lo ´pez Ortiz. She is currently a postdoctoral fellow in Professor Lo ´pez-Ortiz's group with interest in the synthesis of non-natural peptides and peptide analogues.

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“…With the aim of preparing compounds of potential interest for the agrochemical industry, Pryce et al 262 More than 13 years later, a Russian group used a similar approach to synthesize the polyfunctional compounds 339 (Scheme 102). 264 At the same time, Coe et al 265,266 from Pfizer Co. described the preparation of four pyridines 344a−c, 348 and two pyridones 351a,b analogues of (−)-cytisine, assuming that their constrained structures should improve the specific interactions with nicotinic receptors. Their elegant strategy employed an intramolecular Heck reaction to generate the tricyclic structure of their targets.…”

Section: Pyridine Analogues Of (−)-Cytisinementioning

confidence: 99%

“…More than 13 years later, a Russian group used a similar approach to synthesize the polyfunctional compounds 339 (Scheme ) . At the same time, Coe et al , from Pfizer Co. described the preparation of four pyridines 344a – c , 348 and two pyridones 351a , b analogues of (−)-cytisine, assuming that their constrained structures should improve the specific interactions with nicotinic receptors.…”

Section: Synthesis Of Cytisine-inspired Compoundsmentioning

confidence: 99%