Some reactions of 1,2‐dihydropyridines with cyanogen azide. Synthesis of üiazabieyclo[4.1.0]hept‐4‐enes | Zendy

Ondrus T. A. | Zendy; Knaus E. E. | Zendy; Ciam C. S. | Zendy

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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 .

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