A-Pyrrolidinone

The reaction of nitrones with allenes produced three main products an azepine, a pyrrolidinone and an isoxazolidine (Scheme 155) (79JOC4213). The intramolecular cycloaddition of nitrones (529) produced different products depending on the length of n (Scheme 156) (78H(10)257). 

In the course of a study of structure-based design and synthesis of a potent matrix metallo-proteinase-13 inhibitor based on a pyrrolidinone scaffold, the Suzuki coupling reaction of a,/ -unsaturated /-lactam iodide (40) with 4-methoxyphenylboronic acid was carried out to give the corresponding coupling product in 77 % yield (Eq. (76)) [119]. 

One of the first compounds prepared (compound 1, Figure 6.13) was indeed found to lower blood pressure in hypertensive rats by a direct peripheral vasodilator mechanism no (3-blocking activity was observed. Optimization of the activity led to the 6-cyano-4-pyrrolidinylbenzopyran (compound 2), which was more than a 100-fold potent than the nitro derivative. The replacement of the pyrrolidine by a pyrrolidinone (which is the active metabolite) produced a 3-fold increase in activity and the optical resolution led to the (-)-3R, 45 enantiomer of cromakalim (BRL 38227) that concentrates almost exclusively the hypotensive activity." " " ... 

Scheme 5.13 Three-component synthesis of a pyrrolidinone-fused 6-azaindoline.

Pyroxylic spirit. See Methyl alcohol Pyroxylin Pyroxylin plastic Pyroxylin rods. See Nitrocellulose 2-Pyrrolidinone a-Pyrrolidinone. See 2-Pyrrolldone 2-Pyrrolidinone, 1-cyclohexyl-. See N-Cyclohexyl pyrrolldone 2-Pyrrolidinone, 1-dodecyl-. See Lauryl pyrrolldone 2-Pyrrolidinone, 1-ethenyl-, polymer with ethenylbenzene 2-Pyrrolidinone, 1-vinyl-, polymer with styrene. See Styrene/PVP copolymer Pyrrolldone. See 2-Pyrrolldone... 

A solution of epoxy acetate 54 (2.07 g, 7.39 mmol, 1.2 equiv.) in 2-methyl-A-pyrrolidinone (17 mL) was added via cannula to a reaction vessel containing Pd2(dba)3 (677 mg, 0.739 mmol, 0.12 equiv) and flame dried LiCl (1.25 g, 29.6 mmol, 4.7 equiv.) at 25 °C. A 3 mL wash of 2-methyl-A-pyrrolidinone was used to quantitate the transfer. A solution of stannane 53 (2.90 g, 6.31 mmol, 1.0 equiv) and i-Pr2NEt (2.58 mL, 14.8 mmol, 2.3 equiv.) in 2-methyl-A-pyrrolidinone (17 mL) was then added via cannula, again using a 3 mL wash of 2-methyl-A-pyrrolidinone to quantitate the transfer. The resultant dark red solution was stirred at 25 °C for 10 min, and then was warmed to 35 °C and stirred for an additional 1.5 h. Upon completion, the reaction contents were cooled to 25 °C, poured into saturated... 

Synonyms 4-Aminobutyric acid lactam y-Aminobutyric acid lactam y-Aminobu-tyric lactam y-Aminobutyrolactam Butyrolactam y-Butyrolactam LAM 2-Oxopy-rrolidine 2-Pyrol 2-Pyrrolidinone a-Pyrrolidinone Pyrrolidone Pyrrolidone-2 a-Pyrrolidone Empirical C4H7NO Formula CH2CH2CH2C(0)NH... 

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