Synthesis and transformations of ethyl (2E)-3-N,N-dimethylamino-2-(5-ethoxy-1-phenyl-1H-pyrazol-3-yl)propenoate

The reaction of amines (4a-g) with ethyl (2E)-3-N,N-dimethylamino-2-(5-ethoxy-1-phenyl-1H-pyrazol-3-yl)propenoate (3), prepared in two steps from ethyl (4,5-dihydro-5-oxo-1-phenyl-1H-pyrazol-3-yl)acetate (1), gave ethyl (2E)-2-(5-ethoxy-1-phenyl-1H-pyrazol-3-yl)-3-(substituted amino)propenoates (5a-...

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Bibliographic Details
Published inHeterocycles Vol. 66; pp. 207 - 218
Main Authors Bevk, D, Golic, L, Golobic, A, Svete, J, Stanovnik, B
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 31.12.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
3-heteroaryl-1H-pyrazole
STEREOSELECTIVE-SYNTHESIS
3-pyrazol-3-yipropenoate
APLYSINOPSIN ANALOGS
1H-pyrazole
3-(DIMETHYLAMINO)PROPENOATES
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Summary:The reaction of amines (4a-g) with ethyl (2E)-3-N,N-dimethylamino-2-(5-ethoxy-1-phenyl-1H-pyrazol-3-yl)propenoate (3), prepared in two steps from ethyl (4,5-dihydro-5-oxo-1-phenyl-1H-pyrazol-3-yl)acetate (1), gave ethyl (2E)-2-(5-ethoxy-1-phenyl-1H-pyrazol-3-yl)-3-(substituted amino)propenoates (5a-g). The reaction of compound (3) with 2-aminopyridine (4h), 3 amino-1H-pyrazole (4i), 2H-pyran-2-one (6a), and 5,5-dimethylcyclohexane-1,3-dione (6b) afforded 3-(pyrazol-3-yl)pyridopyrimidinone (7a), 6-(pyrazol-3-yl)pyridopyrimidinone (7b), 3-(pyrazol-3-yl)pyranopyrandione (7c), and 3-(pyrazol-3-yl)chromenedione (7d), respectively.
ISSN:0385-5414
1881-0942
DOI:10.3987/COM-05-S(K)1