Synthesis of quinoline derivatives involving hydride transfer

Tilak, B. D.; Ravindranathan, T.; Subbaswami, K. N.

doi:10.1016/s0040-4039(00)76278-2

Cited by 11 publications

(7 citation statements)

References 7 publications

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“…Thus, 1 H NMR spectra contain the corresponding signals for each type of proton, and the integration of these signals is in agreement with the proposed structure. In the case of β-arylamino ketones (5) and (6) (9)- (11) derived from 4′-hydroxyacetophenone) have been attributed to the phenolic proton in these compounds' structure.…”

Section: G Romansupporting

confidence: 84%

“…Treatment of such β-arylamino ketones with polyphosphoric acid 1,2 or hydrochloric acid 2 in ethanol afforded a mixture of quinoline and the corresponding 1,2,3,4-tetrahydroquinoline through disproportionation of the intermediate 1,2-dihydroquinoline; however, only quinolines were isolated when an oxidant such as trityl chloride was added. 1 The use of tin(IV) chloride (either alone, 3 or in the presence of zinc chloride 4 ) or iron(III) chloride 5 in similar reactions also led to quinoline derivatives. In addition, in the presence of a mixture of acetic and sulfuric acids, various analogous 2-[(phenylamino)-(phenyl)methyl]cycloalkanones gave quinolines having saturated rings of variable size fused onto the c side of the heterocyclic system.…”

Section: Introductionmentioning

confidence: 99%

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Novel Phenolic 1-aryl-3-arylamino-1-propanones: Synthesis and Characterization

Roman¹

2017

Acta Chemica Iasi

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A small collection of 1-aryl-3-arylamino-1-propanones having a phenolic moiety in their structure has been obtained by the replacement of the tertiary amino group in ketonic Mannich bases with (hetero)aromatic amines. The installment of the phenolic moiety took place either through the N-alkylation of 4-aminophenol with ketonic Mannich base hydrochlorides, or via amine exchange in ketonic Mannich bases derived from either 2′-hydroxyacetophenone or 4′-hydroxyacetophenone.

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Section: G Romansupporting

confidence: 84%

Section: Introductionmentioning

confidence: 99%

Novel Phenolic 1-aryl-3-arylamino-1-propanones: Synthesis and Characterization

Roman¹

2017

Acta Chemica Iasi

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“…In particular, ketonic tert-Mannich bases and their quaternary salts have been employed frequently as potential intermediates in the synthesis of a multitude of heterocycles of pharmaceutical interest, such as pyrazolines [9 -11], pyridines [3], piperidines [14 -16], 1,5-benzo-or 1,5-hetero-diazepines [16 -19], and quinolines [20]. The use of secMannich bases as synthetic intermediates has been reported in a limited number of cases for the synthesis of pyrimidines [21], quinolines [22,23] and isoquinolines [24,25], and recently we reported [16] the synthesis of the 2H-1,2,4-triazepine ring system starting with ketonic sec-amine bases.…”

Section: Introductionmentioning

confidence: 99%

Mannich Bases as Synthetic Intermediates: Convenient Synthesis of Functionalized 1,2,4-Triazepines, 1,4-Diazepines and 1,5-Diazocines

Afsah

Keshk

Abdel-Rahman

et al. 2011

Zeitschrift Für Naturforschung B

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Transamination between the ketonic Mannich bases 1a, b and primary arylamines gave a series of ketonic sec-Mannich bases 2a -h. A variety of tetrahydro-1,2,4-triazepines 3a -f have been synthesized by treating the arylhydrazones of 2 with formaldehyde. A similar reaction with the benzenesulfonylhydrazone of 2b afforded 4. The 3-styryl-2H-1,2,4-triazepine 5 was obtained from the phenylhydrazone of 2a and cinnamaldehyde. Treatment of arylhydrazones of the 4-methoxystyryl keto base 7 with formaldehyde and cinnamaldehyde afforded the 3,4,5,6-tetrahydro-2H-1,2,4-triazepines 8a, b. Mannich reaction with 4-(p-hydroxyphenyl)-tetrahydro-1,2,4-triazepine 3d afforded the Mannich bases 9, 10 and 11.The reaction of 1b with o-phenylenediamine leads to the 1,5-benzodiazepine 13. The new tetrahydro-1,4-diazepine and tetrahydro-1,5-diazocine Mannich bases 15 and 17 were obtained from 1b and ethylenediamine or 1,3-diaminopropane, respectively. The bi(piperidine) derivative 19 was obtained from 1a and 1,3-diaminopropane.

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“…These results are similar to those described in the synthesis of partially reduced lepidine by cyclization. 19 No evidence for a dihydrointermediate could be obtained for the cyclization.…”

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confidence: 99%

“…No C-alkylated product was detected. Attempts to cause a Claisen-type rearrangement of the vinyl allyl ether27 by heating 19 gave only the dealkylated product 13.…”

mentioning

confidence: 99%