Investigations in heterocycles. VIII. Quinazolines and pyrimidines

deStevens, George; Halamandaris, Angelina; Wenk, Patricia; Mull, R.A.; Schlittler, E.

doi:10.1016/0003-9861(59)90018-9

Cited by 16 publications

(7 citation statements)

References 16 publications

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“…It probably formed by rearrangement of 9. A similar rearrangement, observed in this laboratory, consists in the conversion of ethyl 2-(2-hydroxyethylthio) acetoacetate (11) to ethyl (2-acetoxyethy1thio)acetate (12) in the presence of sodium ethylate (eq. 2).…”

supporting

confidence: 62%

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Ring Opening of Dihydro-1,4-oxathiins

Corbeil¹,

Curcumelli-Rodostamo²,

Fanning³

et al. 1973

Can. J. Chem.

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Acid hydrolysis of 5,6-dihydro-2-methyl-I,4-oxathiin-3-carboxanilide gives 2-(2-hydroxyethy1thio)-acetoacetanilide enol. 3-Carbonyl-substituted 5.6-dihydro-l,4-oxathiins were found to undergo ring cleavage by nucleophilic nitrogen attack on C-2. Thus the following reactions were observed: 3-acetyl-5,6-dihydro-2-methyl-1,4-oxathiin o n treatment with hydrazine gives 4-(2-hydroxyethylthi0)-3,5-dimethylpyrazole, instead of the hydrazone. The 1,4-oxathiins, N-(5,6-dihydro-2-methyl-1,4-oxathiin-3-ylcarbony1)-N'-phenylurea and 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxylic acid hydrazide rearrange to give 5-(2-hydroxyethy1thio)-6-methyl-I-phenylracil and 4-(2-hydroxyethy1thio)-3-methyl-2-pyrazolin-5-one, respectively. Finally, treatment of 5,6-dihydro-2-methyl-1,4-oxathiin-3-carbonyl chloride with 2-aminopyridine and with 2-aminopyrimidine affords 4H-3-(2-hydroxyethy1thio)-2-methylpyrido[l,2-nlpyrimidin-4-one and 4H-3-(2-hydroxyethylthio)-2-methylpyrimido[l,2-a]pyrimidin-4-one, respectively, a s the predominant products.

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supporting

confidence: 62%

“…A strong band in the i.r. spectrum (KBr) between 2400 and 2900 cm-', ascribed by D e Stevens and co-workers (12) to the pyrazolinone zwitterion, shows the important contribution of the tautomeric form 19.…”

Section: Ch3cooch2ch2sch2cooc2h5 12mentioning

confidence: 86%

Ring Opening of Dihydro-1,4-oxathiins

Corbeil¹,

Curcumelli-Rodostamo²,

Fanning³

et al. 1973

Can. J. Chem.

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“…Reactions were also performed at 130°C and 140°C, however, best results were obtained at 145°C. The compound (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18) was further purified by column chromatography (50-65% ethyl acetate in hexane). The time of irradiation and observed yield of the compounds are listed in Table 1.…”

Section: Procedures For the Products A) General Procedures (Compound ...mentioning

confidence: 99%

Direct Chemoselective Synthesis of N-3-Substituted Pyrimidinones in a Microwave-Assisted Method

Laxminarayana

Kundu

2015

Synthetic Communications

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“…However, these substances were completely devoid of activity, thus re-enforcing the original hypothesis that the carbonyl group should be between a nitrogen and another hetero atom within the cyclic system. Finally, it was of interest to prepare some 5,6,7,8-tetrahydroquinazolines and 6,7-dihydro-5-cyclopentapyrimidines [16] (See Figure 8 for the latter series). None of the substances prepared within this class exhibited analgetic properties.…”

Section: Naoch3mentioning

confidence: 99%