Direct alkylation of pyridazines and related compounds by organolithium reagents

Synlett

Volumn , Issue 7, 1998, Pages 762-764

  Piaz, Vittorio Dal ^a   Capperucci, Antonella ^b  

^a UNIVERSITY OF FLORENCE   (Italy)

^b Dipartimento di Chimica   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010251601     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (27)

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19. +, 12), 255 (5), 228 (3), 187 (100).
20. As suggested by one referee, treatment with mild oxidative agent (dry air), after quenching with TMSCl, indeed led to a cleaner reaction, avoiding the formation of products 3 and increasing 2a yield (61%). This behaviour could be consistent with a mechanism based on the substituted dihydro intermediate oxidation (cfr. Wakefield, B.J. in Organolithium Methods, Academic Press, London, 1988, pag. 58-60). Following another referee's suggestion, quenching was done with methyl iodide: no traces of N-methyl derivatives of 3 have been evidenced, ruling out a 1,4-addition.
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22. 313 gave s-Bu-substituted γ-keto acid, which finally was cyclocondensed with methyl hydrazine into the 4-s-butyl-6-phenyl-4,5-dihydro-3(2H)-pyridazinone (overall yield ca. 10%). This compound showed the same spectroscopic data (NMR and GC/MS) as product 8a.
23. Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Ishihara, Y.; Maroyama, K. J. Org. Chem. 1982, 47, 191.
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27. Nakamura, H.; Alzawa, M.; Murai, A. Synlett 1996, 1015.