Synthesis and stereochemical structures of novel spiro[benzocycloheptene-6(5H), 3 '-[3H]pyrazol]-5-ones

Reaction of a variety of 6-arylmethylene-6,7,8,9-tetrahydro-5H-benzoeycloheptene-5-ones 1a-f with nitrilimines (generated in situ by triethylamine dehydrohalogenation of the corresponding hydrazonoyl chlorides 2) in refluxing benzene, afforded the corresponding spiro[benzocycloheptene-6(5H),3'-...

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Bibliographic Details
Published inJournal of chemical research Vol. 2006; no. 2; pp. 81 - 83
Main Author Girgis, AS
Format Journal Article
LanguageEnglish
Published ST ALBANS Science Reviews Ltd 01.02.2006
Sage Publications Ltd
Subjects
Benzene
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
MONOAMINE-OXIDASE
ALKENES
HETEROCYCLES
spiro[benzocycloheptene-6(5H)-3 '-[3H]pyrazol]-5-ones
OPTICAL BRIGHTENERS
REACTIVITY
1,3-dipolar cycloaddition reactions
CHARGE-TRANSFER
6-arylmethylene-6,7.8.9-tetrahydro-5H-benzocycloheptene-5-ones
nitrilimines
3,5-DIARYL PYRAZOLINES
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Summary:Reaction of a variety of 6-arylmethylene-6,7,8,9-tetrahydro-5H-benzoeycloheptene-5-ones 1a-f with nitrilimines (generated in situ by triethylamine dehydrohalogenation of the corresponding hydrazonoyl chlorides 2) in refluxing benzene, afforded the corresponding spiro[benzocycloheptene-6(5H),3'-[3H]pyrazol]-5-ones 3a-h and not the isomeric forms spiro[benzocycloheptene-6(5H),4'-[4H]pyrazol]-5-ones 4 in a highly regioselective manner. The stereochemical configuration of the isolated products was established to be 3'R, 4'S based on single crystal X-ray diffraction of 3a.
Bibliography:ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-1
content type line 23
ISSN:0308-2342
1747-5198
2047-6507
DOI:10.3184/030823406776330837