A new route to N-aryl 2-alkenamides, N-allyl N-aryl 2-alkenamides, and N-aryl alpha,beta-unsaturated gamma-lactams from N-aryl 3-(phenylsulfonyl)propanamides

Citation
Ec. Wang et al., A new route to N-aryl 2-alkenamides, N-allyl N-aryl 2-alkenamides, and N-aryl alpha,beta-unsaturated gamma-lactams from N-aryl 3-(phenylsulfonyl)propanamides, J CHIN CHEM, 48(1), 2001, pp. 83-90
Citations number
29
Categorie Soggetti
Chemistry
Journal title
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
ISSN journal
00094536 → ACNP
Volume
48
Issue
1
Year of publication
2001
Pages
83 - 90
Database
ISI
SICI code
0009-4536(200102)48:1<83:ANRTN2>2.0.ZU;2-L
Abstract
A series of N-aryl 2-alkenamides were produced efficiently by treating N-ar yl 3-(phenylsulfonyl)propanamides with potassium tert-butoxide in THF at 0 degrees C. Without isolation, it was further treated with an additional equ ivalent of potassium tert-butoxide and allyl bromide to give N-allyl N-aryl 2-alkenamides in one pot in good yields. Followed by a ring-closing metath esis reaction, these N-allyl N-aryl 2-alkenamides were respectively convert ed into corresponding N-aryl alpha,beta -unsaturated gamma -lactams in mode rate yields.