UNUSUAL REACTIONS OF L-4-(N,N-DIMETHYLAMINOMETHYLENE)-2-OXAZOLIN-5-ONES WITH O-NUCLEOPHILES - SYNTHESIS OF 2-ARYL-4-HYDROXYMETHYLENE-2-OXAZOLIN-5-ONES

Authors
SINGH KK SINGH RS SINGH RM
Citation
Kk. Singh et al., UNUSUAL REACTIONS OF L-4-(N,N-DIMETHYLAMINOMETHYLENE)-2-OXAZOLIN-5-ONES WITH O-NUCLEOPHILES - SYNTHESIS OF 2-ARYL-4-HYDROXYMETHYLENE-2-OXAZOLIN-5-ONES, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 37(2), 1998, pp. 120-126
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry → ACNP
ISSN journal
03764699
Volume
37
Issue
2
Year of publication
1998
Pages
120 - 126
Database
ISI
SICI code
0376-4699(1998)37:2<120:UROL>2.0.ZU;2-Q
Abstract
The reactions of l-4-(N,N-dimethylaminomethylene)-2-oxazolin-5-ones 2 with aqueous or ethanolic KOH and sodium ethoxide lead to the formatio n of 2-aryl-4-hydroxymethylene-2-oxazolin-5-ones 4, 1,5-bond remaining unaffected. However, the reactions of 2 with aqueous or methanolic KO H afford methyl 2-acylamino-3-dimethylaminopropenoates 9 along with 4. These observations are explained by the hard-soft acid-base (HSAB) pr inciple. Further, compounds 9 on treatment with POCl3 in pyridine and ethanolic KOH give the corresponding cyclized products 2 and 4, respec tively.