Novel potassium channel openers. Part 4: transformation of the 1,4-benzoxazine skeleton into 1,4-benzothiazine, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroquinoxaline, indoline, and 1,5-benzoxazepine

Matsumoto, Yuzo; Tsuzuki, Ryuji; Matsuhisa, Akira; Yoden, Toru; Yamagiwa, Yoko; Yanagisawa, Isao; Shibanuma, Tadao; Nohira, Hiroyuki

doi:10.1016/s0968-0896(99)00292-8

Cited by 49 publications

(24 citation statements)

References 27 publications

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“…[11][12][13][14] The compounds are especially useful as pharmacodynamic agents to suit various applications, especially as anticonvulsant and central nervous system (CNS) depressants. [15][16][17] Very few reports exist in the literature which deals with the LC properties of medium-sized heterocyclic compounds. Five-and six-member heterocyclic rings have been used to attain some LC properties due to the range of structures and known chemistry.…”

Section: Introductionmentioning

confidence: 99%

Novel oxazepinedione-derived symmetric dimers: synthesis and mesophase characterisation of seven-membered heterocyclic compounds

et al. 2016

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The synthesis and characterisation of three sets of symmetric dimeric compounds composed of seven-membered oxazepinedione heterocyclic rings were carried out. All the dimers possess the tetradecyl-(n = 14) alkyl side chain attached to the nitrogen atom of the oxazepinedione core. The oxazepinedione core in turn was connected with varied connecting spacers (n = 4, 6, 8, 10 and 12). The dimers were spectroscopically characterised by FT-IR, 1 H-NMR, 13 C-NMR and elemental analysis techniques. The compounds were investigated for liquid crystalline properties using differential scanning calorimetry and polarising optical microscopy with heating assembly. The precursor imines 2a-e itself started exhibiting liquid crystalline SmA/tilted hexatic mesophase. Further fusion of 2a-e with maleic anhydride, succinic anhydride and phthalic anhydride gave the novel oxazepinedione-derived symmetric dimers 3a-e, 4a-e and 5a-e respectively. The dimers 3a-e and 4a-e did not exhibit any liquid crystal (LC) properties. However, the phthalic anhydride-fused oxazepinediones 5a-e show monotropic nematic liquid crystalline phase. The results indicate that the formation of mesophase is dependent on the type of fused oxazepinedione ring. ARTICLE HISTORY

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Section: Introductionmentioning

confidence: 99%

Novel oxazepinedione-derived symmetric dimers: synthesis and mesophase characterisation of seven-membered heterocyclic compounds

et al. 2016

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“…17,18 The N-alkylation of 2,3-dihydro-1,5-benzoxazepin-4(5H)-one type compounds had been reported. [19][20][21] Our interest in [1,3]oxazepine-4,7-dione molecules arise from our earlier observation of other heterocyclic molecules which have liquid crystalline properties. 22 This has encouraged us to build a new seven-membered ring from easily acquired starting materials.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of New 3‐(3‐Hydroxyphenyl)‐4‐ alkyl‐3,4‐dihydrobenzo[e][1,3]oxazepine‐1,5‐dione Compounds

et al. 2011

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A series of 3-(3-hydroxyphenyl)-4-alkyl-3,4-dihydrobenzo[e][1,3]oxazepine-1,5-dione compounds with general formula C n H 2n＋1 CNO(CO) 2 C 6 H 4 (C 6 H 4 OH) in which n are even parity numbers from 2 to 18. The structure determinations on these compounds were performed by FT-IR spectroscopy which indicated that the terminal alkyl chain attached to the oxazepine ring was fully extended. Conformational analysis in DMSO at ambient temperature was carried out for the first time via high resolution 1 H NMR and 13 C NMR spectroscopy.

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“…[4] Furthermore, they have been reported to open calcium channels; [5] or serve as highly selective antagonists for diverse receptors, for example Kinin B 1 , which is associated with inflammation and pain in septicemia.…”

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confidence: 99%

The First General, Efficient and Highly Enantioselective Reduction of Quinoxalines and Quinoxalinones

Rueping

Tato

Schoepke

2010

Chemistry A European J

192

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Mit Erythrozyten als Templat lassen sich Polymeroberflächen prägen (siehe Rasterkraftmikroskopie‐Aufnahme). Trotz der hohen Flexibilität dieser Zellen zeigen die Abdrücke eine beträchtliche Selektivität für die verschiedenen Blutgruppen, wie aus den Sensorantworten mit der Quarzmikrowaage (Einschub) hervorgeht. So werden durch den Prägeprozess selektive synthetische Antikörper für die Erythrozytenantigene erzeugt.

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Novel potassium channel openers. Part 4: transformation of the 1,4-benzoxazine skeleton into 1,4-benzothiazine, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroquinoxaline, indoline, and 1,5-benzoxazepine

Cited by 49 publications

References 27 publications

Novel oxazepinedione-derived symmetric dimers: synthesis and mesophase characterisation of seven-membered heterocyclic compounds

Novel oxazepinedione-derived symmetric dimers: synthesis and mesophase characterisation of seven-membered heterocyclic compounds

Synthesis and Characterization of New 3‐(3‐Hydroxyphenyl)‐4‐ alkyl‐3,4‐dihydrobenzo[e][1,3]oxazepine‐1,5‐dione Compounds

The First General, Efficient and Highly Enantioselective Reduction of Quinoxalines and Quinoxalinones

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