TY - JOUR
T1 - Improved routes to homologated isoxazoles
AU - Meikrantz, Scott B.
AU - Smith, Miles P.
AU - Xia, Xiongbing
AU - Natale, Nicholas R.
N1 - Funding Information:
We thank National Institutes of General Medical Sciences, Grant #l-R15-GM42029-01 and the National Science Foundation, Experimental Program to Stimulate Competitive Research, Grant ## Rll-8902065 for financial support.
PY - 1994/2/1
Y1 - 1994/2/1
N2 - Two carbon homologation of isoxazole-4-carbinols was performed by reaction of lithio-2,4,4-trimethyl-∆2-oxazoline 1 with 4-chloromethyl-isoxazole 2, followed by trans-esterification and reduction to the isoxazole-4-propanols 5a and b. Alternatively, 2,4-diketones 6 were alkylated with l-bromo-3-chloro-propane, and the chloro ketones 7 treated with hydroxylamine to give isoxazole-4-propanols, 5a-c.
AB - Two carbon homologation of isoxazole-4-carbinols was performed by reaction of lithio-2,4,4-trimethyl-∆2-oxazoline 1 with 4-chloromethyl-isoxazole 2, followed by trans-esterification and reduction to the isoxazole-4-propanols 5a and b. Alternatively, 2,4-diketones 6 were alkylated with l-bromo-3-chloro-propane, and the chloro ketones 7 treated with hydroxylamine to give isoxazole-4-propanols, 5a-c.
UR - http://www.scopus.com/inward/record.url?scp=0028212740&partnerID=8YFLogxK
U2 - 10.1080/00397919408011199
DO - 10.1080/00397919408011199
M3 - Article
AN - SCOPUS:0028212740
SN - 0039-7911
VL - 24
SP - 399
EP - 407
JO - Synthetic Communications
JF - Synthetic Communications
IS - 3
ER -