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Regioselective monometalation of 2,5-pyridinedicarboxamides with (2,2,6,6-tetramethylpiperidino)magnesium chloride (TMPMgCI) (1995)

Schlecker, Wolfgang ; Huth, Andreas ; Ottow, Eckhard ; [weitere]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1995 (1995), S. 1441-1446

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ISSN: 0947-3440

Schlagwort(e): Magnesiation, ortho ; Regioselective ortho metalation ; 2,5-Pyridinedicarboxamides ; (2,2,6,6-Tetramethylpiperidino)magnesium chloride ; Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: The 2,5-pyridinecarboxamides 9-15 were synthesized in one or two steps from diester 1 by addition of an excess of dimethylaluminium amide or successive addition of two different dimethylaluminium amides with or without intermediate workup. For the carboxamides 16 and 17 this method failed; they were, however, available by other procedures. Metalation of the carboxamides 9-17 with TMPMgCI and subsequent reaction with electrophiles led to the 2,3,5- and 2,4,5-substituted pyridines 9a/b-17a/b, 18 and 19 with regioselectivities ranging from predominant 4-substitution to complete 3-substitution.

Zusätzliches Material: 2 Tab.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/jlac.1995199508195

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