Synthesis and chemistry of 1-methyl-3-imino-4-hydroxy-4-phenyl-6-chloro-1,2,3,4-tetrahydroquinoline-2-one

Podešva, C.; Vagi, K.; Solomon, Carola

doi:10.1139/v68-368

Cited by 9 publications

(6 citation statements)

References 1 publication

(1 reference statement)

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“…6 In general, ammonolysis of chloro derivatives (2) with aqueous ammonia has been shown to yield the corresponding 3-hydroxyquinoline-2,4(1H,3H)-diones, and only 3-benzyl substituted 3-chloroquinoline-2,4(1H,3H)-diones (2, R 2 = Bn) afforded the desired 3-amino derivative in low yield. 6 In general, ammonolysis of chloro derivatives (2) with aqueous ammonia has been shown to yield the corresponding 3-hydroxyquinoline-2,4(1H,3H)-diones, and only 3-benzyl substituted 3-chloroquinoline-2,4(1H,3H)-diones (2, R 2 = Bn) afforded the desired 3-amino derivative in low yield.…”

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confidence: 99%

Syntheses of 3-Aminoquinoline- 2,4(1H,3H)-diones

Klásek¹,

Kafka²,

Polis³

et al. 2002

HETEROCYCLES

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Reaction of 3-chloro-(2) and 3-bromoquinoline-2,4(1H,3H)-diones(3) with excess of primary alkyl-or arylamines in dimethylformamide provides the corresponding 3-alkyl-or 3-arylamino derivatives (4). Compounds (4) with the primary amino group at the 3 position were best prepared by reaction of 2 with in situ generated ammonia under anhydrous conditions. An alternative approach to the primary amines (4) via reduction of 3-azidoquinoline-2,4(1H,3H)-diones (5) was investigated. The reduction of 5 with zinc in acetic acid gave moderate to good yields of the desired products, while the reaction with triphenylphosphine afforded exclusively 4-hydroxyquinolin-2(1H)-one (1). Recently, we have demonstrated interesting chemical transformations of 3-hydroxyquinoline-2,4(1H,3H)diones (A, Chart). For example, Wittig olefination of A with ethyl (triphenylphosphoranylidene)acetate proceeded highly stereoselectively to afford E-4-ethoxycarbonylmethylene derivatives (B). 1 In some cases furo[2,3-c]quinoline-2,4(3aH,5H)-diones (C) were obtained, presumably as a result of lactonization of the minor formed Z-4-isomer of B. The structure of C was confirmed by an independent synthesis via the intramolecular Wittig reaction. 2 On the other hand, under the same reaction conditions as described for the synthesis of B, 5,8-disubstituted 3-hydroxyquinoline-2,4(1H,3H)-diones (A) underwent a completely different reaction, yielding primarily products of indoline (D) and benzoxazine (E) structural type. 3 Those have been shown to be formed via the complex molecular rearrangement of A. 4,5The diverse and smooth reactivity of 3-hydroxyquinoline-2,4(1H,3H)-diones (A) prompted us to continue similar studies on the closely related 3-aminoquinoline-2,4(1H,3H)-diones (4). So far, few examples of 4 have been reported in the literature. Those include 3-amino-6-chloro-1-methyl-3-phenylquinoline-

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confidence: 99%

Syntheses of 3-Aminoquinoline- 2,4(1H,3H)-diones

Klásek¹,

Kafka²,

Polis³

et al. 2002

HETEROCYCLES

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“…8), 58 (5), 63 (7), 64 (12), 65 (10), 90 (10), 92 (22), 102 (6), 119 (14), 120 (10), 130 (6), 144 (14), 146 (12), 171 (40), 174 (26), 175 (15), 186 (51), 187 (11), 188 (11), 199 (100), 200 (13), 242 (10). For NMR spectra see Table 1 7), 43 (6), 51 (10), 55 (22), 57 (74), 63 (9), 75 (9), 76 (10), 77 (14), 85 (6), 88 (7), 89 (20), 90 (13), 101 (11), 102 (15), 103 (7), 114 (11), 115 (19), 116 (21), 117 (23), 127 (9), 128 (11), 129 (6), 130 (12), 140 (10), 142 (11), 143 (29), 144 (21), 155 (7), 156 (15), 159 (11), 160 (24), 169 (16), 170 (13), 171 (12), 172 (54), 173 (13), 183 (11), 188 …”

Section: Methods Bunclassified

The Study of Thermal Stability and Morphology of 1-Monoacylglycerols

JaniŠ,

Krejči,

Klàsek

2003

Tenside Surfactants Detergents

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“…Suitable compounds of this type are 3-aminoquinoline-2,4-diones, which is our particular area of interest [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 ]. Even if the occurrence of these compounds in the relevant literature was early rather than rare [ 16 , 17 ], we managed to prepare 3-aminoderivatives using 3-chloroquinolinediones and ammonium salts or primary amines [ 2 ]. Later, we proved that these compounds may also be prepared from 3-hydroxyquinoline-2,4-diones in reaction with ammonia or ammonium salts [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

Molecular Rearrangement of Pyrazino[2,3-c]quinolin-5(6H)-ones during Their Reaction with Isocyanic Acid

Klásek

Lyčka

Křemen

et al. 2022

IJMS

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New tetrahydropyrazino[2,3-c]quinolin-5(6H)-ones were prepared from 3-chloroquinoline-2,4(1H,3H)-diones and ethylene diamine. In their reaction with HNCO, an unprecedented molecular rearrangement produced new types of hydantoin derivatives. All prepared compounds were characterized on the basis of their 1H, 13C, and 15N NMR and ESI mass spectra and some were authenticated by X-ray analysis of single crystalline material. A proposed mechanism for rearrangement is discussed in this essay. The CDK and ABL inhibition activity as well as in vitro cytotoxicity of the prepared compounds was also tested.

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Synthesis and chemistry of 1-methyl-3-imino-4-hydroxy-4-phenyl-6-chloro-1,2,3,4-tetrahydroquinoline-2-one

Cited by 9 publications

References 1 publication

Syntheses of 3-Aminoquinoline- 2,4(1H,3H)-diones

Syntheses of 3-Aminoquinoline- 2,4(1H,3H)-diones

The Study of Thermal Stability and Morphology of 1-Monoacylglycerols

Molecular Rearrangement of Pyrazino[2,3-c]quinolin-5(6H)-ones during Their Reaction with Isocyanic Acid

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