Synthesis of some 7-phenylpyrrolo[1,2-a]pyrimidine derivatives. III. 1987

L Pecori Vettori, and G Auzzi, and F Bruni, and A Costanzo
Dipartimento Di Scienze Farmaceutiche, Università Di Firenze, Italy.

2-Amino-4-phenylpyrrolyl-3-carbonitrile (I) was reacted with ethyl formylacetate sodium salt affording 1,4-dihydro-4-oxo-7-phenylpyrolo[1,2-a]pyrimidin-8-carbonitrile (II), which was alkylated with EtI to give (III), which in turn was hydrolyzed to (IV). Treatment of both (III) and (IV) with 99% H3PO4 at approximately 200 degrees gave 1,4-dihydro-1-ethyl-7-phenylpyrrolo-[1,2-a]pyrimidin-4-one (V) whose structure was ascertained by an unequivocal synthesis starting from (I) and diethyl ethoxymethylenmalonate. Compound (V) was prepared in order to test its pharmacological properties in comparison with 4,7-dihydro-4-ethyl-2-phenylpyrazolo[1,5-a]pyrimidin-7-one, which showed an antiinflammatory activity comparable to that of phenylbutazone and indomethacine, and which was found devoid of ulcerogenic properties.

UI MeSH Term Description Entries
D011743 Pyrimidines A family of 6-membered heterocyclic compounds occurring in nature in a wide variety of forms. They include several nucleic acid constituents (CYTOSINE; THYMINE; and URACIL) and form the basic structure of the barbiturates.
D011758 Pyrroles Azoles of one NITROGEN and two double bonds that have aromatic chemical properties. Pyrrole
D002621 Chemistry A basic science concerned with the composition, structure, and properties of matter; and the reactions that occur between substances and the associated energy exchange.
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D000893 Anti-Inflammatory Agents Substances that reduce or suppress INFLAMMATION. Anti-Inflammatory Agent,Antiinflammatory Agent,Agents, Anti-Inflammatory,Agents, Antiinflammatory,Anti-Inflammatories,Antiinflammatories,Antiinflammatory Agents,Agent, Anti-Inflammatory,Agent, Antiinflammatory,Agents, Anti Inflammatory,Anti Inflammatories,Anti Inflammatory Agent,Anti Inflammatory Agents
D013276 Stomach Ulcer Ulceration of the GASTRIC MUCOSA due to contact with GASTRIC JUICE. It is often associated with HELICOBACTER PYLORI infection or consumption of nonsteroidal anti-inflammatory drugs (NSAIDS). Gastric Ulcer,Gastric Ulcers,Stomach Ulcers,Ulcer, Gastric,Ulcer, Stomach,Ulcers, Gastric,Ulcers, Stomach
D055598 Chemical Phenomena The composition, structure, conformation, and properties of atoms and molecules, and their reaction and interaction processes. Chemical Concepts,Chemical Processes,Physical Chemistry Concepts,Physical Chemistry Processes,Physicochemical Concepts,Physicochemical Phenomena,Physicochemical Processes,Chemical Phenomenon,Chemical Process,Physical Chemistry Phenomena,Physical Chemistry Process,Physicochemical Phenomenon,Physicochemical Process,Chemical Concept,Chemistry Process, Physical,Chemistry Processes, Physical,Concept, Chemical,Concept, Physical Chemistry,Concept, Physicochemical,Concepts, Chemical,Concepts, Physical Chemistry,Concepts, Physicochemical,Phenomena, Chemical,Phenomena, Physical Chemistry,Phenomena, Physicochemical,Phenomenon, Chemical,Phenomenon, Physicochemical,Physical Chemistry Concept,Physicochemical Concept,Process, Chemical,Process, Physical Chemistry,Process, Physicochemical,Processes, Chemical,Processes, Physical Chemistry,Processes, Physicochemical

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