Über Kondensationsprodukte des o‐Phthalaldehyds

Thiele, Johannes; Weitz, Ernst

doi:10.1002/jlac.19103770102

Cited by 62 publications

(15 citation statements)

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“…Several research studies have been reported on the synthesis and properties of 4,5-benzotropones since they were first prepared by Thiele and Weitz nearly a century ago [ 46 – 47 ]. Similar approaches of this method was independently studied by Cook [ 48 ] and Föhlisch [ 49 ] groups.…”

Section: Reviewmentioning

confidence: 99%

One hundred years of benzotropone chemistry

Daştan

Kılıç

Saraçoğlu

2018

Beilstein J. Org. Chem.

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Section: Reviewmentioning

confidence: 99%

One hundred years of benzotropone chemistry

Daştan

Kılıç

Saraçoğlu

2018

Beilstein J. Org. Chem.

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“…In contrast, when o-phthalaldehyde is cyclized with nitromethane/alcoholic potassium hydroxide [67], the reaction product obtained on acidification with mineral acid is not 2-nitro-3-indenol(l22) or its ketone, as would be expected by analogy to (116) 167,781, but instead 2-nitro-l-indenol(124a). This was shown unequivocally by the NMR spectra of compounds (124a)-(124c) [69].…”

Section: )mentioning

confidence: 93%

“…Because of its insolubility in water, one uniform isomer was isolated [16]; of the fourteen theoretically possible configurations (eight meso and six racemic forms), the neo-1, 4-configuration ( 2 ) was assigned to this isomer [17]. with nitromethane, starting with trihydroxy-or aminodihydroxyglutaraldehydes blocked at one aldehyde i 2) group, were described by Grosheinfz and Fisclter [12], with nitromethane and subsequent release of the second Baer and Fischer [14] postulated that direct combina- [*I Abbreviations used: Ac= CH3CO-(acetyl residue); Ms= CH3S02-(mesyl residue).…”

Section: Glyoxalmentioning

confidence: 99%

“…In the preparation of the diethylacetal of (10) from glyoxal semiacetal and nitromethane, he obtained 2,5-dinitrophenol as a by-product. Undoubtedly, under the conditions of the reaction (20 min at 110°C in concentrated potassium carbonate solution), the acetal groups were partially hydrolysed, so that 2,Sdinitrophenol was produced via the intermediates (lo), ( I l l , (2) and subsequent aromatization of (2).…”

Section: 4-dialdehydesmentioning

confidence: 99%

“…The first intermediate in the cyclization of glyoxal with nitromethane is probably 3-nitrolactaldehyde ( l o ) , which may condense either directly via intermediate ( I 1 ) to form (2), or may react with glyoxal to give the intermediate 2,5-dihydroxy-3-nitroglutaraldehyde, which likewise leads via (11) to (2). The aldehyde (10) was in fact prepared by Fischev et al [21,22] and subsequently cyclized in sodium carbonate solution to give a mixture of isomeric dinitroinositols, from which (2) …”

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confidence: 99%

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New Methods of Preparative Organic Chemistry IV. Cyclization of Dialdehydes with Nitromethane

Lichtenthaler

1964

Angew. Chem. Int. Ed. Engl.

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Condensation of nitromethane with suitable diadehydes in alkaline medium provides a general method of cyclization, in which the methyl group of the nitromethane is incorporated into the ring. This method leads to 5‐, 6‐, and 7‐membered rings and is equally applicable to aliphatic, aromatic, and sugar dialdehydes. For example, glyoxal is converted into 1,4‐dideoxy‐1,4‐dinitro‐neo‐inositol, and glutaraldehyde into trans‐2‐nitrocyclohexane‐1,3‐diol, while the corresponding cyclization of xylo‐trihydroxyglutaraldehyde leads to deoxy‐nitroinositols having the scyllo, myo‐1, and muco‐3 configurations.‐In the case of aromatic dialdehydes, the cyclization is accompanied by elimination of water. Thus, phthalaldehyde, naphthalene‐2,3‐dicarboxaldehyde, and homophthalaldehyde yield, respectively, 2‐nitroindenol, 2‐nitrobenzindenol, and 2‐nitronaphthalene. ‐Application of the method to sugar dialdehydes (aldehydic diglycol derivatives of monosaccharides formed by periodate oxidation) constitutes an excellent synthesis of 3‐amino sugars, since 3‐deoxy‐3‐nitropyranoses are formed smoothly on cyclization, and the corresponding 3‐amino derivatives are obtained by hydrogenation. Thus, the reaction sequence: periodate oxidation → cyclization with nitromethane → hydrogenation, leads in the case of α‐and β‐D‐pentosides to 3‐amino‐3‐deoxy‐D‐and‐L‐pentosides, respectively, with ribo, xylo, and arabino configurations. α‐D‐hexosides give derivatives with gluco, manno, and galacto configurations. 3‐Amino‐3,6‐dideoxyglucosides of the D‐and L‐series are obtained from 6‐deoxy‐D‐or‐L‐hexosides, respectively, and 3‐aminohexosans with gulo, ido, and altro configurations are obtained from 1,6‐anhydro sugars. Cyclization of the dialdehydes obtained from sedoheptulose and methyl 4,6‐O‐ethylidene‐α‐D‐glucoside by periodate oxidation, leads to 3‐nitro and, after hydrogenation, to 3‐amino derivatives of 3‐deoxyheptopyranoses.

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