Succinic anhydride treatment

Friedel-Crafts acylation of 3,3-dimethyl-2-indolinone by succinic anhydride gives 3,3-dimethyl-5-(3-catboxyptopionyl)-2-indoline, which is used as an intermediate in the preparation of inotropic agents for treatment of heart failure (94). Antibacterial phlotophenone derivatives have been prepared by Friedel-Crafts acylation with ptopanoyl chlotide (95). 

Hydroxamic acids are an important class of compounds targeted as potential therapeutic agents. A-Fmoc-aminooxy-2-chlorotrityl polystyrene resin 61 allowed the synthesis and subsequent cleavage under mild conditions of both peptidyl and small molecule hydroxamic acids (Fig. 14) [70]. An alternative hydroxylamine linkage 62 was prepared from trityl chloride resin and tV-hydroxyphthalimide followed by treatment with hydrazine at room temperature (Scheme 30) [71]. A series of hydroxamic acids were prepared by the addition of substituted succinic anhydrides to the resin followed by coupling with a variety of amines, and cleavage with HCOOH-THF(l 3). 

Succinic anhydride also may react with protein phenolate side chains of tyrosine residues and the —OH group of aliphatic hydroxy amino acids (Figure 1.82). The phenolate ester derivatives are unstable above pH 5.0, whereas the serine and threonine esters are more stable but may be cleaved by treatment with hydroxylamine at basic pH (Gounaris and Perlman, 1967). 

A thioglycoside was immobilized by the following sequence of reactions. Treatment of the dibutyltin acetal of diol 36 with succinic anhydride afforded 37 in an excellent yield of 85%. Attachment of Fmoc protected glycine to TentaGel hydroxyl resin (38, 0.37 mmol/g resin) under standard conditions followed by removal of the Fmoc group by treatment with piperidine gave polymer 27. Compound 37 was immobilized by amide bond formation with 27 in the presence of... 

A low yield of y-oxo-4-dibenzothiophenebut3rric acid has been obtained by treatment of 4-lithiodibenzothiophene with succinic anhydride. Optimization of this reaction would enable the synthesis of y-oxo-1- and y-oxo-3-dibenzothiophenebutyric acid to be undertaken from the appropriate bromodibenzothiophenes. 

The synthesis of a water-soluble diphenylmethano-bridged fullerene 122 was achieved by hydrolyzing the bis (acetamide) 121 with acetic acid-aqueous hydrochloric acid and then converting it into the bis(succinamide) 122 by treatment with succinic anhydride (Scheme 4.25) [158]. Compound 122 is soluble in water at pH > 7. This is an important requirement for the investigation of the biological activity of fullerenes. Remarkably, 122 is an inhibitor for the HIV enzymes protease (HIV-P) and reverse transcriptase (HIV-RT) [159]. As suggested by molecular modeling. 

Miscellaneous Compounds. A saturated spirocychc pyrrohdine serves as the nucleus for a diamine that has been described as a hypohpemic agent. Treatment of the carbanion of the substituted cylcohexane carboxyhc ester (20-1) with methyl bromoacetate leads to the alkylation and formation of the diester (20-2). Saponification of the ester groups followed by reaction with acetic anhydride leads to ring closure of the succinic anhydride (20-3). Condensation with ammonia leads to the succinimide (20-4). The side chain is then added by alkylation of the anion on nitrogen with l-bromo-4-dimethylaminobutane (20-5). Reaction of this last intermediate with lithium aluminum hydride leads to the reduction of the carbonyl groups to methylene. This affords the pyrrolidine (20-6) atiprimod [22]. 

These data demonstrate that changes in foam properties of liquid cyclone processed cottonseed flour are inducible by treatment with succinic anhydride. Gel electrophoretic and solubility data show that there are alterations in the physical and chemical properties of proteins, and in certain cases these changes improve foam properties, that is, improve solubility and polypeptide dissociation of proteins at the interface of the foaming solution. Similar results have been reported for succinylated soybean and sunflower seed proteins (44. 46). 

A 72 per cent yield of succinic anhydride was obtained by treatment of succinic acid with acetic anhydride according to the method for preparing benzoic anhydride (Org. Syn. 3, 21). 

Reaction of succinic anhydride with benzene in the presence of anhydrous aluminium chloride (slightly over two equivalents see above) yields 3-benzoylpropanoic acid. This may be reduced by the Clemmensen method in the presence of a solvent (toluene) immiscible with the hydrochloric acid to 4-phenylbutanoic acid. Cyclisation to a-tetralone (Expt 6.123) is then effected smoothly by treatment with hot polyphosphoric acid. This reaction sequence represents the first stages in the Haworth procedure for the synthesis of polycyclic aromatic hydrocarbons (see Section 6.1.4, p. 839). 

To complete the total synthesis of the optically active form of veatchine, the successful resolution of the synthetic racemic ketone 244 was accomplished. Compound 244 was reduced stereoselectively with sodium boro-hydride to give the alcohol 248. The latter was heated with succinic anhydride and pyridine in xylene to yield the racemic half-ester 249. Treatment of 249 with brucine afforded the diastereoisomeric brucine salts, which were separated by fractional crystallization. The separated salts were decomposed... 

Figure 5.9 Reaction of wood with alkenyl succinic anhydrides (as in Surfasam treatment)...

Morard M., Vaca-Garcia C., Stevens M., Van Acker J., Pignolet O., Borredon E. Durability improvement of wood by treatment with Methyl Alkenoate Succinic Anhydrides (M-ASA)... 

The conditions used to achieve this transformation vary widely, depending on the nature of the substituent groups. The parent furazan, which had proved elusive for so many years, was first prepared in 1965 by treatment of glyoxime with succinic anhydride at 150-170 °C, followed by distillation (65JOC1854). Monosubstituted furazans are likewise best made by dehydration of the corresponding a-dioximes with acetic anhydride or sulfuric acid. For unsubstituted and all monosubstituted furazans the presence of alkali must be avoided due to their susceptibility to isomerization under these conditions. 

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