From Lactones and Anhydrides

Lactones and anhydrides each react with ammonia or amines to give nitrogen derivatives. In some cases, lactones are converted to lactams and anhydrides to imides. In these cases, hydrolysis will open the ring and generate an amino acid (see 

Just as amines react with esters to form amides, lactones react with amines to give lactams or are opened to give amino acid derivatives directly. When P-propiolactone (2.20) reacted with ammonia, for example, 3-aniinopropanamide (2.2Ia) was obtained. 2 Similar reaction with methylamine gaveno2.2/h but rather a 97% yield of 3-aminopropanoic acid, 2.22. Dimethylamine, however, converted 2.20 to 2.2Ic in 79% yield, along with 13% of 2.22.12 

Reaction of y-butyrolactones with ammonia is a convenient method for preparing ilve-membered ring lactams (2-pyrrolidinone derivatives). When 3-benzyl-7-butyro-lactone (2.23) was heated with ammonia, 4-benzyl-2-pyrrolidinone (2.24) was formed. 13 Hydrolysis led to 3-benzyl-4-aminobutanoic acid (2.25), an anti-spasmodic sedative.l3 Biologically active amino acids are discussed in chapter six. 

Other lactones can also be used. a-Bromo-y-butyrolactone (2.26) was converted to hydroxylactone 2.27.1 jhe lactone ring was opened by potassium phthalimide to give 2.28 and removal of the phthalimido group gave 2-hydroxy-4-aminobutanoic acid (2.29). 

Aminolactone 2.39 (Trt = trityl -CPh3) offered another possibility for synthesis via reduction of the carbonyl moiety, giving a 1 5 mixture of 2.31 2.32. After chromatographic separation of these diastereomers, Wittig oleflnaiionl of 2.31 (via formation of an aldehyde from the hemi-acetal, in situ) gave 2.33 [methyl 4-(N-tritylamino)-6-hydroxyhex-2-enoate] in 80% overall yield.  

---

Chlorination of alcohols by Thionyl Chloride the preparation of acyl chlorides from lactones and anhydrides, and the bromi-nation and iodination of aromatic rings by Benzyltrimethylammo-nium Tribromide and Benzyltrimethylammonium Dichloroio-date, respectively, are all effectively catalyzed by the presence of ZnCl2. In addition, ZnCl2 acts as a source of chloride for the halogenation of primary, secondary, and allylic alcohols using Triphenylphosphine-DiethylAzodicarboxylate. ... 

---