ISSN:
0947-3440
Keywords:
Magnesiation, ortho
;
Regioselective ortho metalation
;
2,5-Pyridinedicarboxamides
;
(2,2,6,6-Tetramethylpiperidino)magnesium chloride
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1995199508195
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