4260-40-6Relevant academic research and scientific papers
Flash vacuum pyrolysis (fvp) of some hexahydroquinazolin-4(1H)-ones
Peláez, Walter J.,Szakonyi, Zsolt,Fül?p, Ferenc,Yranzo, Gloria I.
, p. 1049 - 1057 (2008/09/17)
Some cis/trans-2-thioquinazolin-4-ones and their 2,4-dione analogs were subjected to flash vacuum pyrolysis. The cis- and trans-thio compounds reacted at lower temperatures than the cis- and trans-dioxo analogs, showing a lower thermal stability. All of these compounds afforded similar reactions: ring opening to the corresponding iso(thio)cyanate, the loss of H{radical dot} and {radical dot}NCS to form three isomeric cyclohexadienes and then aromatization to form the corresponding benzamide. The cis-dioxo compound also underwent a competitive retro Diels-Alder (RDA) reaction to form 3-phenylpyrimidine-2,4(1H,3H-dione(3-phenyluracil)) and butadiene. Kinetic measurements of the ring opening reaction supported a concerted β-elimination as the most probable mechanism.
Solid-phase synthesis of 4(1H)-quinolone and pyrimidine derivatives based on a new scaffold - Polymer-bound cyclic malonic acid ester
Huang, Xian,Liu, Zhanxiang
, p. 6731 - 6737 (2007/10/03)
An efficient method for the preparation of polymer-bound cyclic malonic acid ester starting from Merrifield resin has been developed. Reaction of the resin-bound cyclic malonic acid ester with triethyl orthoformate and subsequent double substitution with
ISOLATION OF NEW CHLORINATED REGIOISOMERS OF MONO N-SUBSTITUTED URACIL DERIVATIVES AND SYNTHESIS OF 3-SUBSTITUTED 8-PHENYLPYRIMIDO-1,2,4-TRIAZINE-5,7(6H,8H)-DIONES
Nagamatsu, Tomohisa,Yamasaki, Hirofumi,Yoneda, Fumio
, p. 1147 - 1164 (2007/10/02)
A variety of fervenulin type products, 3-substituted 8-phenylpyrimido-1,2,4-triazine-5,7(6H,8H)-diones (18a-i), were synthesized by nitrosative or nitrative cyclization of the aldehyde hydrazones (17a-i) derived from 6-(1-methylhydrazino)-1-phenyluracil (16) with aliphatic as well as aromatic aldehydes.The compound (16) was prepared by the reaction of 6-chloro-1-phenyluracil (8) with methylhydrazine.In addition, not only the precursor of 16, 6-chloro-1-phenyluracil (8), but also other new chlorinated regioisomers of mono N-substituted pyrimidine (9) and uracil (14) were isolated and characterized by the reductive dechlorination of them.
STEREOCHEMICAL STUDIES 107; SATURATED HETEROCYCLES 111; PREPARATION OF URACILS VIA CYCLOREVERSION OF NORBORNENE-FUSED PYRIMIDINEDIONES
Bernath, Gabor,Stajer, Geza,Szabo, Angela E.,Szoeke-Molnar, Zsolt,Sohar, Pal,et al.
, p. 1921 - 1930 (2007/10/02)
From diexo-norbornane- and norbornene-azetidinones 5 and 6 with aryl isocyanates, N-arylcarbamoyl-substituted β-lactams (9 and 10) were prepared.The structures of the compounds were elucidated by IR, NMR spectroscopy and X-ray analysis, in comparison with saturated methylene-bridged quinazoline-2,4-diones (7a-b) prepared from norbornane-diexo-β-amino acid (1) with isocyanates and PPA.When heated with PPA, compounds 9 can be isomerized to 7.For preparation of the unsaturated compounds 8, the amino acid 2 was converted into the acid amides (13) and cyclized with 1,1'-carbonyl-diimidazole to tricyclic quinazoline-2,4-dione (8a-e), which decompose when heated, splitting off cyclopentadiene to yield 3-substituted uracils (14).
