1939
DOI: 10.1021/jo01213a010
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Abstract: Continuing the investigations in this field which have already appeared from these laboratories,1•2 experiments have been conducted with veratrole derivatives, whose purpose was the synthesis of the true papaverine analog in the quinazoline series. Although this goal has not yet been reached, some interesting reactions and products have been discovered and are here recorded.

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Cited by 29 publications
(12 citation statements)
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“…Therefore we decided to apply the Bogert quinazoline synthesis, as it allowed us to obtain the required intermediate 6-hydroxyquinazoline (39) from inexpensive 3-hydroxybenzaldehyde (36). This special ring condensation method, which was developed by Marston Bogert in the 1930s [34,35] and which is not found often in the literature, starts with the regioselective nitration of 36. The resulting disubstituted benzaldehyde 37 is then converted with formamide under a hydrogen chloride gas stream into the N,N'-diformylated aminal 38, which undergoes reductive cyclization by treatment with zinc in acetic acid to deliver directly the desired building block 39.…”
Section: S: Inhibitors Of Tubulin Polymerizationmentioning
confidence: 99%
“…Therefore we decided to apply the Bogert quinazoline synthesis, as it allowed us to obtain the required intermediate 6-hydroxyquinazoline (39) from inexpensive 3-hydroxybenzaldehyde (36). This special ring condensation method, which was developed by Marston Bogert in the 1930s [34,35] and which is not found often in the literature, starts with the regioselective nitration of 36. The resulting disubstituted benzaldehyde 37 is then converted with formamide under a hydrogen chloride gas stream into the N,N'-diformylated aminal 38, which undergoes reductive cyclization by treatment with zinc in acetic acid to deliver directly the desired building block 39.…”
Section: S: Inhibitors Of Tubulin Polymerizationmentioning
confidence: 99%
“…It was subsequently found that treatment of either of these compounds with ethyl mercaptopyruvate under ambient conditions in the presence of triethylamine resulted in the generation of the thiophene 6 in almost identical yields, suggesting that elimination of HBr from 4 precedes reaction with the thiol. Subsequent attempts to cyclize the amino ketoester 6 to generate the thienopyrrolidinedione 7 proved unsuccessful, a finding consistent with the limited number of reports extant in the literature for this type of vinylogous amide-ester cyclization [21][22][23]. In an attempt to increase the nucleophilicity of the amino functionality in 6, the arylketone moiety was reduced using triethylsilane under acidic conditions [24] to give the aminoester 8 in 77% yield.…”
mentioning
confidence: 76%
“…conventional hydrogenation of nitroesters over Pd or Pd/C provides variable yields of the corresponding amine. 15 Although the described use of the catalyst 2 in the reduction of various organic substrates is quite general, it involves a restricted choice of reaction media. It appears that DMF is the best solvent for such reactions though hydrogenation occurs in ethyl acetate at a slower rate.…”
Section: Methodsmentioning
confidence: 99%