Synthesis of N-[1-acetyl-5-(d-arabino-tetraacetoxybutyl)-2-methyl-3-pyrroyl]-N-phthalimidoacetamide

Sadek, Mohamed M. El; Soccary, Nagwa N. El

doi:10.1016/0008-6215(91)89026-c

Cited by 3 publications

(2 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Another drawback was that these reactions required the use of expensive starting materials. Others have reported the synthesis of N - substituted aminophthalimides using phthalic anhydride and substituted hydrazines as starting materials; however, all these methods required multistep procedures for the synthesis of specific compounds and, in most cases, used extreme reaction conditions. Taking all these factors into account, we were motivated to find alternative synthetic routes which would enable the preparation of a variety of N-substituted aminophthalimides.…”

Section: Resultsmentioning

confidence: 99%

New Synthesis of 1,1-Substituted Hydrazines by Alkylation of N-Acyl- or N-alkyloxycarbonylaminophthalimide Using the Mitsunobu Protocol

2000

View full text Add to dashboard Cite

N-acyl- and N-alkoxycarbonylaminophthalimides are prepared using a convenient reaction and are efficiently used as acid partners in Mitsunobu reaction. This reaction allows them to be alkylated by primary, secondary or benzyl groups. Comparison of the reactivities and pK(a) values of these N-substituted aminophthalimides suggest that the success of the Mitsunobu reaction in this case seems to be governed more by steric than by electronic effects. A final dephthaloylation step results in an efficient method for the preparation of 1,1-substituted hydrazines.

show abstract

Section: Resultsmentioning

confidence: 99%

New Synthesis of 1,1-Substituted Hydrazines by Alkylation of N-Acyl- or N-alkyloxycarbonylaminophthalimide Using the Mitsunobu Protocol

2000

View full text Add to dashboard Cite

show abstract

“…1,3,4-Thiadiazoles are thus a group of heterocycles whose derivatives are important in industry, medicine and agriculture [ 13 , 15 , 16 , 17 , 18 , 19 , 20 , 21 ]. Accordingly, in continuation of our work in this area [ 22 , 23 , 24 , 25 , 26 , 27 ], a variety of heterocyclic derivatives have been prepared from saccharide derivatives, involving some new thiadiazoles, oxathiadiazoles, and their chemistry and effect of the derivatives on the enzyme tyrosinase was studied [ 28 , 29 , 30 , 31 ], which is the rate limiting step in melanin biosynthesis [ 32 ]. In humans, the main role of the melanins is photoprotection of the skin by absorbing UV radiation that causes DNA damage and the formation of reactive oxygen species (ROS).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New 1,3,4-Thiadiazole and 1,2,3,4-Oxathiadiazole Derivatives from Carbohydrate Precursors and Study of Their Effect on Tyrosinase Enzyme

et al. 2012

View full text Add to dashboard Cite

5-(1,2,3,4-Tetrahydroxybutyl)-2-methylfuran-3-carbohydrazide (2) was condensed with a variety of ketones to afford carbohydrazide derivatives 3–6. Acetylation of 3–5 afforded the acetyl derivatives 7–9, while periodate oxidation of 3–6 afforded the formyl derivatives 10–13. Acid catalyzed condensation of thiosemicarbazide or o-tolylthiosemicarbazide with the prepared aldehydes 10–12 gave thiosemicarbazone derivatives 14–19. Cyclization of the latter with acetic anhydride afforded 4,5-dihydro-1,3,4-thiadiazolyl derivatives 20–25. On the other hand, condensation of p-tosylhydrazine with the prepared aldehydes 10–12 afforded p-tosylhydrazone derivatives 26–28. Cyclization of 26–28 with acetic anhydride afforded 1,2,3,4-oxathiadiazole derivatives 29–31 respectively. Moreover, the obtained results regarding to the effect of some of the prepared compounds on tyrosinase enzyme showed that the majority of these compounds having an inhibitory effect; especially compounds 12, 16, 17, and 28.

show abstract

Synthesis and reactions of 5-(d-arabino-tetrahydroxybutyl)-3-(2,3-dihydro-1,3,4-oxadiazole-2-thion-5-yl)-2-methylfuran and 5-(d-arabino-tetrahydroxybutyl)-3-(2-substituted amino-1,3,4-oxadiazol-5-yl)-2-methylfuran

Hassan

Faidallah

El-Massry

et al. 1997

Carbohydrate Research

View full text Add to dashboard Cite

Synthesis of N-[1-acetyl-5-(d-arabino-tetraacetoxybutyl)-2-methyl-3-pyrroyl]-N-phthalimidoacetamide

Cited by 3 publications

References 5 publications

New Synthesis of 1,1-Substituted Hydrazines by Alkylation of N-Acyl- or N-alkyloxycarbonylaminophthalimide Using the Mitsunobu Protocol

New Synthesis of 1,1-Substituted Hydrazines by Alkylation of N-Acyl- or N-alkyloxycarbonylaminophthalimide Using the Mitsunobu Protocol

Synthesis of New 1,3,4-Thiadiazole and 1,2,3,4-Oxathiadiazole Derivatives from Carbohydrate Precursors and Study of Their Effect on Tyrosinase Enzyme

Synthesis and reactions of 5-(d-arabino-tetrahydroxybutyl)-3-(2,3-dihydro-1,3,4-oxadiazole-2-thion-5-yl)-2-methylfuran and 5-(d-arabino-tetrahydroxybutyl)-3-(2-substituted amino-1,3,4-oxadiazol-5-yl)-2-methylfuran

Contact Info

Product

Resources

About