Functionalized buta-1,3-diynyl-N-methylpyrazoles by sequential “diacetylene zipper” and Sonogashira coupling reactions

Abstract

A reaction sequence consisting of the “Diacetylene zipper” of buta-1,3-diynes from internal to terminal isomers, followed by Sonogashira cross-coupling with 3-,4- or 5-iodopyrazoles, was investigated as a new approach to buta-1,3-diynyl-N-methylpyrazoles. Various pyrazoles bearing alkyl and hydroxyalkyl containing buta-1,3-diyne substituents in the 3-,4- or 5-position and functional groups at the neighboring positions of the ring were obtained.

Original language	English
Pages (from-to)	762-765
Number of pages	4
Journal	Tetrahedron Letters
Volume	58
Issue number	8
DOIs	https://doi.org/10.1016/j.tetlet.2017.01.032
Publication status	Published - 1 Jan 2017
Externally published	Yes

Keywords

Buta-1,3-diynes
Diacetylene zipper
Pyrazoles
Sonogashira cross-coupling

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2017.01.032

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title = "Functionalized buta-1,3-diynyl-N-methylpyrazoles by sequential “diacetylene zipper” and Sonogashira coupling reactions",

abstract = "A reaction sequence consisting of the “Diacetylene zipper” of buta-1,3-diynes from internal to terminal isomers, followed by Sonogashira cross-coupling with 3-,4- or 5-iodopyrazoles, was investigated as a new approach to buta-1,3-diynyl-N-methylpyrazoles. Various pyrazoles bearing alkyl and hydroxyalkyl containing buta-1,3-diyne substituents in the 3-,4- or 5-position and functional groups at the neighboring positions of the ring were obtained.",

keywords = "Buta-1,3-diynes, Diacetylene zipper, Pyrazoles, Sonogashira cross-coupling",

author = "Govdi, {Anastasiya I.} and Kulyashova, {Alexandra E.} and Vasilevsky, {Sergey F.} and Balova, {Irina A.}",

year = "2017",

month = jan,

day = "1",

doi = "10.1016/j.tetlet.2017.01.032",

language = "English",

volume = "58",

pages = "762--765",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "8",

}

TY - JOUR

T1 - Functionalized buta-1,3-diynyl-N-methylpyrazoles by sequential “diacetylene zipper” and Sonogashira coupling reactions

AU - Govdi, Anastasiya I.

AU - Kulyashova, Alexandra E.

AU - Vasilevsky, Sergey F.

AU - Balova, Irina A.

PY - 2017/1/1

Y1 - 2017/1/1

N2 - A reaction sequence consisting of the “Diacetylene zipper” of buta-1,3-diynes from internal to terminal isomers, followed by Sonogashira cross-coupling with 3-,4- or 5-iodopyrazoles, was investigated as a new approach to buta-1,3-diynyl-N-methylpyrazoles. Various pyrazoles bearing alkyl and hydroxyalkyl containing buta-1,3-diyne substituents in the 3-,4- or 5-position and functional groups at the neighboring positions of the ring were obtained.

AB - A reaction sequence consisting of the “Diacetylene zipper” of buta-1,3-diynes from internal to terminal isomers, followed by Sonogashira cross-coupling with 3-,4- or 5-iodopyrazoles, was investigated as a new approach to buta-1,3-diynyl-N-methylpyrazoles. Various pyrazoles bearing alkyl and hydroxyalkyl containing buta-1,3-diyne substituents in the 3-,4- or 5-position and functional groups at the neighboring positions of the ring were obtained.

KW - Buta-1,3-diynes

KW - Diacetylene zipper

KW - Pyrazoles

KW - Sonogashira cross-coupling

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U2 - 10.1016/j.tetlet.2017.01.032

DO - 10.1016/j.tetlet.2017.01.032

M3 - Article

AN - SCOPUS:85009796972

VL - 58

SP - 762

EP - 765

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 8

ER -