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Synthesis and theoretical calculations of novel 5‐aryl substituted 2,4,7‐trioxo and 4,7‐dioxo‐2‐thioxopyrido[2,3‐ d ]pyrimidines
Author(s) -
Rodríguez René,
Suárez Margarita,
Ochoa Estael,
Morales Alhmed,
González Leandro,
Martín Nazario,
Quinteiro Margarita,
Seoane Carlos,
Soto José L.
Publication year - 1996
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570330108
Subject(s) - chemistry , moiety , aryl , ethylene , chemical shift , computational chemistry , stereochemistry , substitution (logic) , medicinal chemistry , organic chemistry , alkyl , catalysis , computer science , programming language
New substituted pyrido[2,3‐ d ]pyrimidines 5 and 6 have been prepared in one‐step from the readily available 6‐amino‐2,4‐dioxotetrahydropyrimidine ( 1 ) or 6‐amino‐4‐oxo‐2‐thioxotetrahydropyrimidine ( 2 ) and the arylidene substituted Meldrum's acid. The substitution pattern of the ethylene moiety in compounds 5 and 6 results in a strong push‐pull electronic effect. The semiempirical calculations using the AM1 method reveal two equally favoured conformations showing a distorted geometry. The calculated charge density values confirm the observed 13 C nmr chemical shifts.