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An efficient synthesis of novel sucrose-containing dilactams.

Potopnyk MA, Jarosz S - Monatsh. Chem. (2013)

Bottom Line: An efficient and convenient approach to sucrose-containing dilactams has been developed.The method, based on reaction of regioisomeric 6,6'-di-O-[(aminomethyl)-phenyl]-1',2,3,3',4,4'-hexa-O-methylsucrose with isophtaloyl or 2,6-pyridinedicarbonyl dichlorides, provided the 1:1-macrocycles in good yields. .

View Article: PubMed Central - PubMed

Affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.

ABSTRACT

Abstract: An efficient and convenient approach to sucrose-containing dilactams has been developed. The method, based on reaction of regioisomeric 6,6'-di-O-[(aminomethyl)-phenyl]-1',2,3,3',4,4'-hexa-O-methylsucrose with isophtaloyl or 2,6-pyridinedicarbonyl dichlorides, provided the 1:1-macrocycles in good yields.

Graphical abstract: .

No MeSH data available.


Macrocyclic diamides 10a–10c and 11a–11c
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Fig1: Macrocyclic diamides 10a–10c and 11a–11c

Mentions: 1′,2,3,3′,4,4′-Hexa-O-methyl-6,6′-di-O-(methylsulfonyl)sucrose (1) was treated with 2 equiv. of the appropriate, commercially available cyanophenol (7a–7c; o, m, p, respectively) in DMF in the presence of potassium carbonate to give the corresponding 6,6′-di-O-(cyanophenyl)-1′,2,3,3′,4,4′-hexa-O-methylsucroses (8a–8c) in 81–84 % yield. These compounds were quantitatively converted into the 6,6′-di-O-[(aminomethyl)phenyl]-1′,2,3,3′,4,4′-hexa-O-methylsucroses (9a–9c) by reduction with LiAlH4. The crude bis-amines 9a–9c were subjected to cyclocondensation reaction with isophthaloyl or 2,6-pyridinedicarbonyl dichlorides (5 and 6, respectively) to achieve closure of the ring (Scheme 2). To avoid formation of the dimeric byproducts, the reactions were performed in dilute solution. In all cases a 1:1-product (10a–10c and 11a–11c) was formed in good yield (63–74 %; Fig. 1).Fig. 1


An efficient synthesis of novel sucrose-containing dilactams.

Potopnyk MA, Jarosz S - Monatsh. Chem. (2013)

Macrocyclic diamides 10a–10c and 11a–11c
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4495044&req=5

Fig1: Macrocyclic diamides 10a–10c and 11a–11c
Mentions: 1′,2,3,3′,4,4′-Hexa-O-methyl-6,6′-di-O-(methylsulfonyl)sucrose (1) was treated with 2 equiv. of the appropriate, commercially available cyanophenol (7a–7c; o, m, p, respectively) in DMF in the presence of potassium carbonate to give the corresponding 6,6′-di-O-(cyanophenyl)-1′,2,3,3′,4,4′-hexa-O-methylsucroses (8a–8c) in 81–84 % yield. These compounds were quantitatively converted into the 6,6′-di-O-[(aminomethyl)phenyl]-1′,2,3,3′,4,4′-hexa-O-methylsucroses (9a–9c) by reduction with LiAlH4. The crude bis-amines 9a–9c were subjected to cyclocondensation reaction with isophthaloyl or 2,6-pyridinedicarbonyl dichlorides (5 and 6, respectively) to achieve closure of the ring (Scheme 2). To avoid formation of the dimeric byproducts, the reactions were performed in dilute solution. In all cases a 1:1-product (10a–10c and 11a–11c) was formed in good yield (63–74 %; Fig. 1).Fig. 1

Bottom Line: An efficient and convenient approach to sucrose-containing dilactams has been developed.The method, based on reaction of regioisomeric 6,6'-di-O-[(aminomethyl)-phenyl]-1',2,3,3',4,4'-hexa-O-methylsucrose with isophtaloyl or 2,6-pyridinedicarbonyl dichlorides, provided the 1:1-macrocycles in good yields. .

View Article: PubMed Central - PubMed

Affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.

ABSTRACT

Abstract: An efficient and convenient approach to sucrose-containing dilactams has been developed. The method, based on reaction of regioisomeric 6,6'-di-O-[(aminomethyl)-phenyl]-1',2,3,3',4,4'-hexa-O-methylsucrose with isophtaloyl or 2,6-pyridinedicarbonyl dichlorides, provided the 1:1-macrocycles in good yields.

Graphical abstract: .

No MeSH data available.