J. Z. Brzezinski

The dual behaviour of N,N-dialkylpyridylcarboxyclic amides in the reaction with lithium diisopropylamide

Abstract The dual behaviour of N,N-diisopropylpyridylcarboxylic amides in the reaction with iPr2NLi depending upon temperature and structure of a given amide, is described.

A CONCISE REGIOSELECTIVE SYNTHESIS OF HYDROXYAZAISOINDOLINONES AND THEIR CONVERSION INTO PYRIDOPYRIDAZINONES

Abstract The synthesis of pyridopyridazinones 7 and 8 via the reaction of hydroxyazaisoindolinones 5 and 6 with hydrazine hydrate is described. Compounds 7 and 8 were then subjected to reactions with alkyl halides to furnish N-alkyl derivatives. Only in the reaction of pyridopyridazinone 8 with benzyl bromide was the O-benzylpyridopyridazine 14b formed in addition to the N-benzylpyridopyridazinone 14a .

Application of organolithium and related reagents in synthesis, Part XII. Synthesis of phenyl- and pyridylpyridopyridazinones and their derivatives

SummaryThe preparation of the pyridazinones10a,10b,11a,11b, and12a,12b from the ketoamides7,8, and9 and hydrazine hydrate is described. It was found that from ketoamides8b and9b in addition to the expected pyridopyridazinones11b and12b also aminopyridopyridazines14 and15 were formed and that ketoamide7b gave exclusively aminopyridopyridazine13. The pyridopyridazinones10b,11b, and12b were alkylated with alkyl iodides.ZusammenfassungDie Darstellung der Pyridazinone10a,10b,11a,11b und12a,12b aus Ketoamiden7,8 und9 und Hydrazinhydrat wird beschrieben. Es wurde festgestellt, daß aus Ketoamiden8b und9b außer den erwarteten Pyridopyridazinonen11b und12b auch Aminopyridopyridazine14 und15 enstanden und daß das Ketoamid7b ausschließlich ins Aminopyridopyridazin13 überführt wurde. Die Pyridopyridazinone10b,11b und12b wurden mit Alkyljodiden alkyliert.

The conformational analysis of benzocycloalkanones using the lanthanide induced shift msthod

The conformations of the benzocycloalkanones 1a - 1d in solution were estimated by the use of the lanthanide induced shift method (LIS of 1H, 13C NMR spectra). The starting geometry was obtained from MNDO calculations. The torsional angle of the carbonyl group with respect to the benzene ring is 0° for compound 1a, 3° for 1b, 56° for 1c and 67° for the eight-membered ring compound 1d. These results are compared with the data obtained by other methods for similar compounds and are discussed with regard to kinetic measurements for solvolysis of chlorobenzocycloalkanes and oxidation of benzocycloalkanols, respectively.