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Volumn 13, Issue 6, 2007, Pages 1754-1762

Reduction of different electron-poor N-heteroarylhydrazines in strong basic conditions

Author keywords

Heterocyeles; Hydrazone type tautomery; Hydrodehalo genation; Reaction mechanisms; Regioselectrvity

Indexed keywords

CATALYSIS; REACTION KINETICS; REDUCTION; REGIOSELECTIVITY; SYNTHESIS (CHEMICAL);

EID: 34250657899     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600282     Document Type: Article
Times cited : (16)

References (52)
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    • Compound 1 was synthesized as decribed: A. Unciti-Broceta, M. J. Pineda-de-las-Infantas, J. J. Díaz-Mochón, R. Romagnoli, P. G. Baraldi, M. A. Gallo; A. Espinosa, J. Org. Chem. 2005, 70, 2878-2880.
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    • The reduction was very quick in all the experiments at the corresponding reflux temperature of each alcohol. However, the bigger the substituent R, the longer the time and the higher the temperature needed to complete the reaction
    • The reduction was very quick in all the experiments at the corresponding reflux temperature of each alcohol. However, the bigger the substituent R, the longer the time and the higher the temperature needed to complete the reaction.
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    • The reaction was monitored by HPLC
    • The reaction was monitored by HPLC.
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    • The air present in the solvents was removed by bubbling a stream of nitrogen through the corresponding solvent for 30 min
    • The air present in the solvents was removed by bubbling a stream of nitrogen through the corresponding solvent for 30 min.
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    • According to: D. L. Smith, P. J. Elving, J. Am. Chem. Soc. 1961, 83, 1412-1420; it should be possible to isolate 1,6-dihydropurine before its oxidation into purine by avoiding the exposure to air and neutralizing the reaction mixture.
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    • unpublished results
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    • The heterocyclic systems of the compounds reduced in this article are much more electron-poor than the 2-pyridone ring
    • The heterocyclic systems of the compounds reduced in this article are much more electron-poor than the 2-pyridone ring.
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    • [19] the aromatic heteroaryldiazene derivative would be the expected intermediate produced through a Shapiro-type reduction mechanism in this kind of compounds.
    • [19] the aromatic heteroaryldiazene derivative would be the expected intermediate produced through a Shapiro-type reduction mechanism in this kind of compounds.
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    • For a review of rational and maximal structure proliferation from simple aromatic and heterocyclic starting material, see: M. Schlosser, Angew. Chem. 2005, 117, 380-398;
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.