Convenient and improved halogenation of 3,5-diarylisoxazoles using N-halosuccinimides

Ruth Ann Day; Jacqueline A. Blake; Chad E. Stephens

doi:10.1055/s-2003-40516

Convenient and improved halogenation of 3,5-diarylisoxazoles using N-halosuccinimides

Ruth Ann Day
, Jacqueline A. Blake
, Chad E. Stephens

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

42 Scopus citations

Abstract

The convenient C-4 halogenation of 3,5-diarylisoxazoles using N-halosuccinimides (NBS, NCS, or NIS) in acetic acid is described. A strong acid catalyst was required for efficient halogenation of some isoxazoles depending on the substituent on the 5-phenyl ring. Finally, the 4-iodoisoxazoles were found to undergo a novel proto-deiodination upon heating in the presence of H₂SO₄.

Original language	English (US)
Pages (from-to)	1586-1590
Number of pages	5
Journal	Synthesis
Issue number	10
DOIs	https://doi.org/10.1055/s-2003-40516
State	Published - 2003
Externally published	Yes

Keywords

Halogenation
Iodo cleavage
Isoxazoles
N-halosuccinimides
Solvent effects

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-2003-40516

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title = "Convenient and improved halogenation of 3,5-diarylisoxazoles using N-halosuccinimides",

abstract = "The convenient C-4 halogenation of 3,5-diarylisoxazoles using N-halosuccinimides (NBS, NCS, or NIS) in acetic acid is described. A strong acid catalyst was required for efficient halogenation of some isoxazoles depending on the substituent on the 5-phenyl ring. Finally, the 4-iodoisoxazoles were found to undergo a novel proto-deiodination upon heating in the presence of H2SO4.",

keywords = "Halogenation, Iodo cleavage, Isoxazoles, N-halosuccinimides, Solvent effects",

author = "Day, \{Ruth Ann\} and Blake, \{Jacqueline A.\} and Stephens, \{Chad E.\}",

year = "2003",

doi = "10.1055/s-2003-40516",

language = "English (US)",

pages = "1586--1590",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "10",

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TY - JOUR

T1 - Convenient and improved halogenation of 3,5-diarylisoxazoles using N-halosuccinimides

AU - Day, Ruth Ann

AU - Blake, Jacqueline A.

AU - Stephens, Chad E.

PY - 2003

Y1 - 2003

N2 - The convenient C-4 halogenation of 3,5-diarylisoxazoles using N-halosuccinimides (NBS, NCS, or NIS) in acetic acid is described. A strong acid catalyst was required for efficient halogenation of some isoxazoles depending on the substituent on the 5-phenyl ring. Finally, the 4-iodoisoxazoles were found to undergo a novel proto-deiodination upon heating in the presence of H2SO4.

AB - The convenient C-4 halogenation of 3,5-diarylisoxazoles using N-halosuccinimides (NBS, NCS, or NIS) in acetic acid is described. A strong acid catalyst was required for efficient halogenation of some isoxazoles depending on the substituent on the 5-phenyl ring. Finally, the 4-iodoisoxazoles were found to undergo a novel proto-deiodination upon heating in the presence of H2SO4.

KW - Halogenation

KW - Iodo cleavage

KW - Isoxazoles

KW - N-halosuccinimides

KW - Solvent effects

UR - https://www.scopus.com/pages/publications/0042243698

UR - https://www.scopus.com/pages/publications/0042243698#tab=citedBy

U2 - 10.1055/s-2003-40516

DO - 10.1055/s-2003-40516

M3 - Article

AN - SCOPUS:0042243698

SN - 0039-7881

SP - 1586

EP - 1590

JO - Synthesis

JF - Synthesis

IS - 10

ER -

Convenient and improved halogenation of 3,5-diarylisoxazoles using N-halosuccinimides

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

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