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Some reactions of 1,2‐dihydropyridines with cyanogen azide. Synthesis of üiazabieyclo[4.1.0]hept‐4‐enes
Author(s) -
Ondrus T. A.,
Knaus E. E.,
Ciam C. S.
Publication year - 1979
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570160246
Subject(s) - chemistry , cyanogen , tautomer , yield (engineering) , azide , chloroform , oxide , organic chemistry , medicinal chemistry , metallurgy , materials science
The regiospecific 1,3‐dipolarcycloaddition reaction of 1,2‐dihydropyridines 1 with cyanogen azide 2 afford 2,7‐diazabieyelo[4.1.0]hept‐4‐enes 3 in quantitative yield. Catalytic hydrogenation of 3 gives rise to a tautomeric mixture of piperidylidene‐2‐cyanamides 5 in quantitative yield. Alternatively treatment of 3 with a suspension of alumina oxide in chloroform yields 1,2,5,6‐tetrahydropyridylidenes 4 which are also quantitatively reduced to 5 .