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Some reactions of 1,2-dihydropyridines with organic azides. Synthesis of diazabicylo[4.1.0]hept-4-enes, 1,2,5,6-tetrahydropyridylidene-2-cyan (sulfon, carbon) amides, and piperidylidene-2-cyan (sulfon, carbon) amides
The regiospecific 1,3-dipolarcycloaddition reaction of 1,2-dihydropyridines 1 with organic azides 2 afford 2,7-diazabicyclo[4.1.0]hept-4-enes 4 , whereas solutions of 1 also containing lithium hydroxide give predominately 4 along with the diazo product 6 . In contrast, the dimeric product 7 was obta...
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| Published in: | Canadian journal of chemistry 1979-09, Vol.57 (18), p.2342-2349 |
|---|---|
| Main Authors: | , , |
| Format: | Article |
| Language: | English |
| Citations: | Items that cite this one |
| Online Access: | Get full text |
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| Summary: | The regiospecific 1,3-dipolarcycloaddition reaction of 1,2-dihydropyridines
1
with organic azides
2
afford 2,7-diazabicyclo[4.1.0]hept-4-enes
4
, whereas solutions of
1
also containing lithium hydroxide give predominately
4
along with the diazo product
6
. In contrast, the dimeric product
7
was obtained from the reaction of
1
a with hydrazoic acid. Catalytic hydrogenation of
4
gives rise to a tautomeric mixture of
9
and
10
; when R
2
is methanesulfonyl or p-aminobenzenesulfonyl only
9
was obtained. Treatment of
4
with neutral alumina gives rise to the 1,2,5,6-tetrahydropyridylidenes
8
which are likewise reduced to a mixture of
9
and
10
or
9
. |
|---|---|
| ISSN: | 0008-4042 1480-3291 |
| DOI: | 10.1139/v79-377 |