COMPETITIVE INTRAMOLECULAR AMINOLYSIS - RELATIVE RATES OF 5-MEMBERED AND 6-MEMBERED LACTAM RING-CLOSURE

Authors
PATTERSON KH DEPREE GJ ZENDER JA MORRIS PJ
Citation
Kh. Patterson et al., COMPETITIVE INTRAMOLECULAR AMINOLYSIS - RELATIVE RATES OF 5-MEMBERED AND 6-MEMBERED LACTAM RING-CLOSURE, Tetrahedron letters, 35(2), 1994, pp. 281-284
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
2
Year of publication
1994
Pages
281 - 284
Database
ISI
SICI code
0040-4039(1994)35:2<281:CIA-RR>2.0.ZU;2-H
Abstract
Methyl 4,5-diaminopentanoate (4,5-Dape Me) undergoes competitive intra molecular aminolysis to 5-aminomethyl-2-pyrrolidinone (L5) and 5-amino -2-piperidinone (L6) in dilute alkaline aqueous solution at 25 degrees C. Use of this single compound provides an ideal case for assessing t he relative rates of 5- and 6-membered lactam ring closure. Assessment s are also made using the intramolecular aminolysis of pairs of compou nds: methyl 2,4-diaminobutanoate (2,4-Dab Me) and methyl 2,5-diaminope ntanoate (25-Dape Me); methyl 4-aminobutanoate (4-Ab Me) and methyl 5- aminopentanoate (5-Ape Me).