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Reactions of Pyridine Analogues of Aza‐ ortho ‐xylylenes Generated from 1,3‐Dialkylpyridosultams
Author(s) -
Kosinski Szymon,
Wojciechowski Krzysztof
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200004)2000:7<1263::aid-ejoc1263>3.0.co;2-e
Subject(s) - chemistry , pyridine , derivative (finance) , alkylation , ring (chemistry) , hydrogen , extrusion , medicinal chemistry , polymer chemistry , organic chemistry , catalysis , materials science , financial economics , economics , metallurgy
2,3‐Dihydro‐3‐imino‐2‐methylenepyridines, generated by thermal extrusion of SO 2 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 SO 2 , 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.