Improved routes to homologated isoxazoles

Scott B. Meikrantz; Miles P. Smith; Xiongbing Xia; Nicholas R. Natale

doi:10.1080/00397919408011199

Improved routes to homologated isoxazoles

Scott B. Meikrantz, Miles P. Smith, Xiongbing Xia, Nicholas R. Natale

University of Idaho

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	399-407
Number of pages	9
Journal	Synthetic Communications
Volume	24
Issue number	3
DOIs	https://doi.org/10.1080/00397919408011199
State	Published - Feb 1 1994

Funding

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.

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#l-R15-GM42029-01

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10.1080/00397919408011199

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title = "Improved routes to homologated isoxazoles",

abstract = "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.",

author = "Meikrantz, \{Scott B.\} and Smith, \{Miles P.\} and Xiongbing Xia and Natale, \{Nicholas R.\}",

note = "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.",

year = "1994",

month = feb,

day = "1",

doi = "10.1080/00397919408011199",

language = "English",

volume = "24",

pages = "399--407",

journal = "Synthetic Communications",

issn = "0039-7911",

publisher = "Taylor and Francis Ltd.",

number = "3",

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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 - https://www.scopus.com/pages/publications/0028212740

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 -

Improved routes to homologated isoxazoles

Abstract

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