Hydrolysis of<i>N</i>-Substituted Phthalimides Using Anion Exchange Resins. Synthesis of Hydroxy-Substituted Aliphatic Primary Amines (Amino Alcohols)

Kuriyama, Naohiro; Inoue, Yoshiharu; Kitagawa, Keishi

doi:10.1055/s-1990-27000

Cited by 8 publications

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“…The exact nature of these ring‐opened products was not established. Use of anion exchange resins,22 partial reduction with NaBH 4 in acidic medium followed by heating at reflux,23 or treatment with n ‐butylamine24 or methylamine25 similarly led to complex mixtures of unidentified products. Ultimately, cleavage of the phthalimide groups of 24 – 29 , 30 , and 32 with hydrazine [Eq.…”

Section: Resultsmentioning

confidence: 99%

Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Aminobicyclo[5.1.0]octitols

El‐Mansy

Flister

Lindeman

et al. 2015

Chemistry A European J

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A series of eight stereoisomeric N-(tetrahydroxy bicyclo-[5.1.0]oct-2S*-yl)phthalimides were prepared in one to four steps from N-(bicyclo[5.1.0]octa-3,5-dien-2-yl)phthalimide (±)-7, which is readily available from cyclooctatetraene (62 % yield). The structural assignments of the stereoisomers were established by 1 H NMR spectral data as well as X-ray crystal structures for certain members. The outcomes of several epoxydiol hydrolyses, particularly ring contraction and enlargement, are of note. The isomeric phthalimides as well as the free amines did not exhibit β-glucosidase inhibitory activity at a concentration of less than 100 μM.

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Section: Resultsmentioning

confidence: 99%

Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Aminobicyclo[5.1.0]octitols

El‐Mansy

Flister

Lindeman

et al. 2015

Chemistry A European J

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Protection for the Amino Group

Wuts

Greene²

2006

Greene's Protective Groups in Organic Synthesis

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Protection for the Amino Group

2014

Greene's Protective Groups in Organic Synthesis

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CARBAMATES 907Carbamate Derived from an Amine and CO 2 , 908 Methyl and Ethyl, 909 9-Fluorenylmethyl, 912 2,6-Di-t-butyl-9-fluorenylmethyl, 915 2,7-Bis (trimethylsilyl)fluorenylmethyl, 915 2-(2-Ethylhexyl)-9-fluorenylmethyl, 915 2,7-Bis-(2-ethylhexyl)-9-fluorenylmethyl, 915 9-(2-Sulfo)fluorenylmethyl, 916 9-(2,7-Dibromo)fluorenylmethyl, 916 17-Tetrabenzo[a,c,g,i]fluorenylmethyl, 916 2-Chloro-3-indenylmethyl, 916 Benz[f]inden-3-ylmethyl, 916 1,1-Dioxobenzo[b]thiophene-2-ylmethyl, 917 2,7-Di-t-butyl[9-(10,10-dioxo-10,10,10,10-tetrahydrothioxanthyl)]methyl, 917 Azidomethyl, 920 2-(Hydroxymethyl)-3-phenyl-4H-1-benzothiopyran-4-one 1,1-Dioxide, 920 2-Methylsulfonyl-3-phenyl-1-prop-2-enyloxy, 920 Substituted Ethyl Carbamates 921 2,2,2-Trichloroethyl, 921 2-Trimethylsilylethyl, 923 (2-Phenyl-2-trimethylsilyl)ethyl, 925 2-(Triphenylsilyl)ethyl, 925 2-Phenylethyl, 927 2-Chloroethyl, 927 2 3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decyl, 927 1,1-Dimethyl-2-haloethyl, 927 1,1-Dimethyl-2,2-dibromoethyl, 927 1,1-Dimethyl-2,2,2-trichloroethyl, 928 2-(2´and 4´-Pyridyl)ethyl, 928

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Hydrolysis ofN-Substituted Phthalimides Using Anion Exchange Resins. Synthesis of Hydroxy-Substituted Aliphatic Primary Amines (Amino Alcohols)

Cited by 8 publications

References 0 publications

Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Aminobicyclo[5.1.0]octitols

Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Aminobicyclo[5.1.0]octitols

Protection for the Amino Group

Protection for the Amino Group

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