ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The dihydropyran 3 reacts with sulfonyl azides to give the known (sulfonylimino)-ethers ( = lactone sul-fonylimines) 4 and 18. Reaction of 4 with NH2NH2 · H2O leads to the aminoiriazole-dibulanol 5, characterized as its tetraacetate 8, and not, as previously claimed, to 6 or 7. Similarly, the dihydrofuran-derived (tosylimino)-ether 10 yields 11 The structure of 5 was established by X-ray analysis, and a mechanism for its formation is proposed. Reaction of 4 with NH2NMe2 afforded the lactone hydrazone 16 and the hydrazidine 17. Catalysis by imidazole suppressed the formation of 17similarly, the [(trifluoromethyl)sulfonyl]imine 18 yielded 16, and, by reaction with NH2N(Me)Ph or 4-amino-4H-1,2,4-triazole, the lactone hydrazone 19 and the adduct 20, respectively. The 1,4-lactone hydrazone 21 was obtained from 10 or from 22. The structure of 20 was established by X-ray analysis. Treatment of 16 with BuLi followed by BnBr yielded the α-alkylated lactone hydrazone 23.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19910740837
