1979
DOI: 10.1248/cpb.27.1287
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Chemistry of salicylic acid and anthranilic acid. IV. Synthesis of 6-chloro-5-sulfamoyl- and 6-chloro-3-sulfamoylanthranilic acid derivatives.

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Cited by 18 publications
(6 citation statements)
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“…In contrast to the widely studied 2,3-dihydroquinazolinones, [16][17][18][19][20][21][22][23][24][25][26][27][28][29] sporadic literature is available [30][31][32][33][34] for the synthesis of 1-H-spiro[isoindoline-1,2quinazoline]-3,4 (3 H)-diones. They are generally synthesized by multi-component reaction of isatoic anhydride, amine and carbonyl compounds or two component cyclocondensation of anthranilamide with carbonyl compounds.…”
Section: Introductionmentioning
confidence: 99%
“…In contrast to the widely studied 2,3-dihydroquinazolinones, [16][17][18][19][20][21][22][23][24][25][26][27][28][29] sporadic literature is available [30][31][32][33][34] for the synthesis of 1-H-spiro[isoindoline-1,2quinazoline]-3,4 (3 H)-diones. They are generally synthesized by multi-component reaction of isatoic anhydride, amine and carbonyl compounds or two component cyclocondensation of anthranilamide with carbonyl compounds.…”
Section: Introductionmentioning
confidence: 99%
“…Considering the availability of potential starting materials, we focused on the oxidation of the corresponding 4-halo-2-nitrotoluenes. A typical KMnO 4 oxidation in water afforded a 35% yield after 4 days at refluxing temperature with 6 equiv of KMnO 4 added in batches (Table , entry 1). Various common modifications of the KMnO 4 oxidation, such as the addition of cosolvents or the employment of phase-transfer reagents, were largely unsuccessful (Table , entries 2−7).…”
Section: Resultsmentioning
confidence: 99%
“…The cyclocondensation with the aldehyde in the presence of p -toluenesulfonic acid, in refluxing MeOH, gave the respective DHQ. 231 The copper-catalyzed cyclocondensation of 2-halobenzamide and aldehyde in the presence of aqueous ammonia, 232 and 2-halobenzamide with anilines, 233 also gave DHQs derivatives. DHQs could also be prepared by reduction from 4(3 H )-quinazolinones (QZs) with NaBH 4 , 234,235 or NaBH 4 CN.…”
Section: Introductionmentioning
confidence: 99%