Regioselective Metalation of Ortho-Aminopicolines Using the Pivaloyl Group as a Directing Group: Synthesis of Naphthyridines
- 1 February 1993
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 23 (3), 365-372
- https://doi.org/10.1080/00397919308009790
Abstract
2-(1,3-Dioxan-2-yl)-3-methyl-4- and 2-chloro-3,4-dimethyl-5-pivaloylaminopyridines were prepared and converted to 1,6- and 1,7-naphthyridines via regioselective lithiation of the ortho-methyl group, reaction with 2,2-diethoxyacetophenone and subsequent acid-catalyzed cyclization.Keywords
This publication has 9 references indexed in Scilit:
- Convergent synthesis of the streptonigrin alkaloid skeleton. Directed orthometalation connection to aryl-aryl cross-couplingTetrahedron, 1992
- Directed ortho metalation. Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromaticsChemical Reviews, 1990
- A general approach to the synthesis of 1,6-, 1,7-, and 1,8-naphthyridinesThe Journal of Organic Chemistry, 1990
- Synthesis of ortho‐substituted aminopyridines. Metalation of pivaloylamino derivativesJournal of Heterocyclic Chemistry, 1989
- Regiospecific electrophilic substitution of aminopyridines: ortho lithiation of 2-, 3-, and 4-(pivaloylamino)pyridinesThe Journal of Organic Chemistry, 1983
- Regioselective metalation reactions of some substituted (methoxymethoxy)arenesThe Journal of Organic Chemistry, 1982
- Regioselective metalation of the 4-position of pyridine. New and convenient alkylation and acylation of 3-amino-5-methoxypyridineThe Journal of Organic Chemistry, 1981
- Studies on anticoccidial agents. 12. Synthesis and anticoccidial activity of methyl-2(6)-nitro- and -3(5)-nitropyridinecarboxamidesJournal of Medicinal Chemistry, 1978
- Syntheses of Heterocyclic Compounds of Nitrogen. CXVIIIYAKUGAKU ZASSHI, 1959