Reaction glutaric anhydride

SAMs of OH-terrninated alkanethiols have been used in many surface modification reactions (Fig. 14). These reacted with OTS to yield a weU-ordered bdayer (322), with octadecyldimethylchlorosilane (323,324), with POCI3 (325—327), with trifluoroacetic anhydride (328), epichlorohydrin (329), with alkyhsothiocyanate (330), with glutaric anhydride (331), and with chlorosulfonic acid (327). 

As shown in Scheme 32, 3-substituted glutaric anhydrides 209 are excellent substrates for reaction with amidox-... 

Our final example is that of cyclic anhydrides, namely prochiral 3-sub-stituted glutaric anhydrides (7.101, R = Me, Et, or Pr). When incubated with lipase in an inert solvent in the presence of an alcohol (methanol, butan-l-ol, etc.), these compounds underwent nucleophilic ring opening with formation of a hemiester (7.102) of (/ -configuration (60-90% ee) [180]. This product enantioselectivity and, of course, the lack of reactivity in the absence of lipase show the enzymatic nature of the reaction. 

These methods parallel the synthesis just described for the five-membered rings. As indicated in structures (42)—(49), standard reactions of aliphatic chemistry can be extended to the preparation of piperidines, tetrahydropyrans and pentamethylene sulfides (44 Z = N, O, S) glutarimides, glutaric anhydrides and glutaric thioanhydrides (46 Z = N, O, S) and 8-lactams, 8-lactones and 8-thiolactones (49 Z = N, O, S). 

There is the 3 methods for preparing of 8-azaspiro(4.5)decane-7,9-dione, 8-(4-(4-(2-pyrimidinyl)-l-piperazinyl)butyl) monohydrochloride (U.S. Patent 3,717,634). One of them is follows a mixture of 0.1 mole of the substituted glutaric anhydride, 0.1 mole of l-(4-aminobutyl)-4-(2-pyrimidinyl)piperazine (U.S. Pat. 3,398151), and 300 ml of pyridine was refluxed until imide formation was completed. The degree of reaction was readily followed by taking an aliquot portion of the reaction mixture, removing the solvent, and obtaining the infrared absorption spectrum of the residue. When reaction is complete, the spectrum exhibited typical infrared imide bands at 1701 and 1710 cm-1 whereas if incomplete, the infrared spectrum contains amide and carboxyl absorption bands at 1680, 1760 and 3300 cm 1. 

The selenium analogue of glutaric anhydride 153 has been prepared by reaction of glutaryl chloride with seleno-4-toluamide 152 in the presence of triethylamine (Equation 61) <1999CL485>. A significantly lower yield of 153 was obtained without added base. 

Reaction of succinylhydrazide derived from (A)-amino-2-methoymethylpyrrolidine (SAMP) with benzylmagne-sium chlorides allows us to prepare a number of enantiopure 5-arylmethyl-pyrrolidones and -pyrrolidines.265 An enantioselective desymmetrization of anhydrides was reported by Fu. Arylmagnesium chlorides react in toluene in the presence of 1 equiv. of (—)-sparteine with 3-substituted glutaric anhydrides, giving aryl ketones with 87-92% ee (Scheme 90).266... 

Phenol, btomobenzene, i-butylbenzene, and acenaphthene give keto acids in good yields. The reaction is applicable to other aliphatic dibasic acid anhydrides like glutaric anhydride, adipic poly anhydride, and maleic anhydride, furnishing w-aroyl acids. An excellent discussion including experimental conditions and procedures has been given. Optimum conditions for the reaction of naphthalene, biphenyl, and chlorobenzene with phthalic anhydride have been determined. The Corresponding keto acids are obtained in 90-98% yields. In this type of condensation, nitrobenzene is stated to be far superior to other solvents with respect to solvent power and ability to slow side reactions. ... 

In the synthesis of (S)-zearalenone and of a chiral spiroac-etal, (2S,6/ )-2-methyl-l,7-dioxaspiro[5.6]dodecane, the starting product was a functionalized 3-keto sulfoxide resulting from the reaction of glutaric anhydride with lithiated (+)-(7 )-methyl p-tolyl sulfoxide (eq 6). 

LiAlH4) of the product afforded an aminomethylquinolizidine (19) which, on reaction with glutaric anhydride followed by acetic anhydride, afforded ( )-lamprolobine (20).2 2... 

Other derivatives from carboxylic acids can be used as substrates in Friedel-Crafts acylation reactions, including anhydrides and esters. Toluene reacted with glutaric anhydride in the presence of aluminum chloride to give 197, which was used in the Vig et al. synthesis of curcumene ether.128 Lactones are also effective substrates in this cyclization, generating ketones. 129... 

Sulfur tetrafluoride and F2 gas are among other fluorinating agents used for the synthesis of fluorinated ethers. For example, F-oxane was reported to form in the reaction of anhydride of F-glutaric acid or F-glutaryl fluoride with excess of SF4. Perfluorinated spiro-ethers 19 were prepared in high yield by exhaustive fluorination of the parent hydrocarbons using elemental fluorine. 

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