Monoquaternary neuromuscular blocking agents based on 1-tetralone and 1-indanone

Biggs, David F.; Casy, A. F.; Chu, Ih; Coutts, Ronald T.

doi:10.1021/jm00226a004

Cited by 22 publications

(15 citation statements)

References 6 publications

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“…The one-pot synthesis of 6-amino-1-tetralone 60 was attempted using the method reported by Mizuno et al [79] The 1 H NMR spectrum of 60, comparison of the melting point (129-131 • C, lit. [80] 129-130 • C) and electrospray ionization (ESI) mass spectrometry all confirmed formation of 60. Conversion of the 6-amino-1-tetralone 60 to 52 was achieved under the Sandmeyer conditions (45% yield).…”

Section: Mechanistic Discussion: Beckmann Rearrangementmentioning

confidence: 92%

The Application of the Schmidt Reaction and Beckmann Rearrangement to the Synthesis of Bicyclic Lactams: Some Mechanistic Considerations

2010

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The syntheses of some methoxy-substituted bicyclic lactams, of the types 3 and 4, are reported employing two different conditions for the Schmidt reaction of appropriate ketones and employing two different conditions for the Beckmann rearrangement of the corresponding ketoximes. The alkyl to aryl migration ratios of the reactions were determined by high-performance liquid chromatography analysis of the reactions. The mechanisms of the reactions reported are discussed, some limitations of the reported mechanisms identified, and an alternative mechanism proposed in light of the outcomes of the various reactions. Application of the Schmidt reaction and Beckmann rearrangement was used for the synthesis of some chloro bicyclic lactams, of the types 3 and 4.

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Section: Mechanistic Discussion: Beckmann Rearrangementmentioning

confidence: 92%

The Application of the Schmidt Reaction and Beckmann Rearrangement to the Synthesis of Bicyclic Lactams: Some Mechanistic Considerations

2010

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“…10 cm) and the filtrate was concentrated. The residue was purified by flash chromatography (silica gel 200-400 mesh, 50% EtOAc in hexanes) affording 11 41 (0.708 g, 4.39 mmol, 84%), as a brown solid (mp: 137.7-137.8 °C), together with 7-amino-1,2,3,4-tetrahydronaphthalen-1-ol (0.0976 g, 0.598 mmol, 11%), also as a brown solid.…”

Section: Methodsmentioning

confidence: 99%

“…The reaction was quenched with H 2 O, extracted with AcOEt, washed with brine, and dried over anhydrous MgSO 4 . The solvent was removed under reduced pressure giving 12 41 (0.326 g, 1.60 mmol, 99%), as a yellow solid (mp 161.0-161.1 °C). (13) and 5-bromo-1-tetralone (14).…”

Section: -Amino-1-tetralonementioning

confidence: 99%

“…The resulting brown oil was purified by flash chromatography (silica gel 200-400 mesh, 5% EtOAc and 5% Et 2 O in hexanes) affording the indan 41 (0.139 g, 0.512 mmol, 35%), 42 (0.073 g, 0.269 mmol, 18%), 43 (0.010 g, 0.037 mmol, 3%), 44 (0.0796 g, 0.264 mmol, 18%) and 45 (0.0264 g, 0.128 mmol, 9%). (41). cis-5-Bromo-1,2,3,4-tetrahydro-1,2-dimethoxynaphthalene (43).…”

Section: -Bromonaphthalenementioning

confidence: 99%

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Thallium trinitrate-mediated ring contraction of 1,2-dihydronaphthalenes: the effect of electron-donating and electron-withdrawing groups

Silva

Sousa

Ferraz

et al. 2005

J. Braz. Chem. Soc.

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A oxidação de uma série de 1,2-diidronaftalenos, substituídos no anel aromático, foi investigada com trinitrato de tálio (TTN) em metanol ou em trimetilortoformiato (TMOF) como solvente. Em todos os casos, indanos foram formados, embora o rendimento tenha variado de excelente a baixo, dependendo da estrutura do substrato. A presença de um grupo doador de elétrons no substrato favorece o rearranjo, enquanto que uma quantidade significativa de derivados glicólicos, bem como naftalenos, foi obtida na oxidação de 1,2-diidronaftalenos com um grupo retirador de elétrons, tais como Br e NO 2 . Mecanismos para a formação de cada um destes produtos foram propostos.The oxidation of a series of 1,2-dihydronaphthalenes substituted in the aromatic ring was investigated with thallium trinitrate (TTN) in methanol or in trimethylorthoformate (TMOF) as solvent. In all cases, indans are produced, although the yield varied from excellent to poor, depending on the structure of the substrate. The presence of an electron-donating group in the substrate favors the rearrangement, whereas significant amounts of glycolic derivatives, as well as naphthalenes, were obtained in the oxidation of 1,2-dihydronaphthalenes bearing electron-withdrawing groups, such as Br and NO 2 . Mechanisms for the formation of each of these products are proposed.ring contraction reaction. The present article describes a detailed study of the TTN-mediated oxidation of 1,2dihydronaphthalenes bearing different groups in the aromatic ring (Me, OMe, OH, NH 2 , NHAc, Br and NO 2 ), better defining the scope of this reaction, which will facilitate future applications. In addition, a more clear picture of the mechanism of the thallium(III)-mediated oxidation of olefins could be drawn based on the new results.

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“…For related literature, see: Allen (2002); Biggs et al (1976); Bruno et al (2004); Rambaldi et al (2001).…”

Section: Related Literaturementioning

confidence: 99%

5,6,7-Trimethoxy-2,3-dihydroinden-1-one

Saeed

Bolte

2007

Acta Cryst E

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Monoquaternary neuromuscular blocking agents based on 1-tetralone and 1-indanone

Cited by 22 publications

References 6 publications

The Application of the Schmidt Reaction and Beckmann Rearrangement to the Synthesis of Bicyclic Lactams: Some Mechanistic Considerations

The Application of the Schmidt Reaction and Beckmann Rearrangement to the Synthesis of Bicyclic Lactams: Some Mechanistic Considerations

Thallium trinitrate-mediated ring contraction of 1,2-dihydronaphthalenes: the effect of electron-donating and electron-withdrawing groups

5,6,7-Trimethoxy-2,3-dihydroinden-1-one

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