ISSN:
1434-193X
Keywords:
Alkenes
;
Nitrogen heterocycles
;
Pericyclic reactions
;
Rearrangements
;
Spiro compounds
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
-2,3-Dihydro-3-imino-2-methylenepyridines, generated by thermal extrusion of SO2 from 1,3-dialkyl-1,3-dihydroisothiazolo[4,3-b]pyridine 2,2-dioxides (1,3-dialkylpyridosultams), underwent [1,5] hydrogen shifts, which led to 3-alkylamino-2-vinylpyridine derivatives. Cycloalkanespiro-3-pyridosultams 12, which were easily obtained by alkylation of pyridosultams with α,ω-dihaloalkanes, gave, in a similar reaction, 3-alkylamino-2-cycloalkenylpyridine derivatives 14 in good yields. Cyclobutanespiro-3-pyridosultam 12b, after thermal extrusion of SO2, formed cyclobutenyl derivative 14b, which underwent a ring-opening reaction to form butadiene derivative 15. The latter can be trapped with dienophiles, for example, N-phenylmaleimide.
Type of Medium:
Electronic Resource
