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Synthesis of Some New Spiro, Isolated and Fused Heterocycles Based on 1 H ‐indole‐2‐One
The reaction of 3‐benzoylcyanomethylidine‐1( H )‐indole‐2‐one ( 1 ) with a variety of active methylene compounds, thioglycolic acid, glycine, hydrazine hydrate and phenyl hydrazine led to the formation of compounds 4a‐d‐10 . 3‐Thiosemicarbazide‐1( H )‐indole‐2‐one 2 on reaction with α‐halocarbonyl c...
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| Published in: | Journal of the Chinese Chemical Society (Taipei) 2001-10, Vol.48 (5), p.921-927 |
|---|---|
| Main Authors: | , , |
| Format: | Article |
| Language: | English |
| Citations: | Items that this one cites Items that cite this one |
| Online Access: | Get full text |
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| Summary: | The reaction of 3‐benzoylcyanomethylidine‐1(
H
)‐indole‐2‐one (
1
) with a variety of active methylene compounds, thioglycolic acid, glycine, hydrazine hydrate and phenyl hydrazine led to the formation of compounds
4a‐d‐10
. 3‐Thiosemicarbazide‐1(
H
)‐indole‐2‐one
2
on reaction with α‐halocarbonyl compounds gave compounds
11a‐c, 12a‐c
. The latter compounds on heating with phosphoryl chloride, cyclization takes place
via
losing water to give the angular tetracyclic compounds
13a,b
and
14a‐c
. Cyanoacetic hydrazone derivative
3
readily cyclized upon heating in triethyl orthoformate to give the tricyclic system, oxopyridazino indole
15
.
On the other hand, the reaction of
3
with benzylidine malononitrile and benzylidene ethylcyanoactate gave the pyranyl hydrazone derivatives
16a,b
. |
|---|---|
| ISSN: | 0009-4536 2192-6549 |
| DOI: | 10.1002/jccs.200100134 |