Hexamethyldisilazane-promoted sonogashira reaction of polyfunctionalized N-containing heterocycles

Masahiko Inouye; Yasuhiro Doi; Junichi Azuchi; Wataru Shirato; Junya Chiba; Hajime Abe

doi:10.3987/COM-10-S(E)89

Hexamethyldisilazane-promoted sonogashira reaction of polyfunctionalized N-containing heterocycles

Masahiko Inouye^*, Yasuhiro Doi, Junichi Azuchi, Wataru Shirato, Junya Chiba, Hajime Abe

^*Corresponding author for this work

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

9 Scopus citations

Abstract

1,1,1,3,3,3-Hexamethyldisilazane (HMDS) was found to be an efficient solvent for Sonogashira reaction. For the synthesis of C-nucleosides, Sonogashira reaction of ethynyldeoxyriboside with halogenated pyrimidine or pyridine derivatives could be improved by the use of an HMDS-DMF mixed solvent. In situ protection of hydroxy and amino groups by the solvent system may play an important role for the improvement.

Original language	English
Pages (from-to)	1137-1141
Number of pages	5
Journal	Heterocycles
Volume	82
Issue number	2
DOIs	https://doi.org/10.3987/COM-10-S(E)89
State	Published - 2010/02/28

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "Hexamethyldisilazane-promoted sonogashira reaction of polyfunctionalized N-containing heterocycles",

abstract = "1,1,1,3,3,3-Hexamethyldisilazane (HMDS) was found to be an efficient solvent for Sonogashira reaction. For the synthesis of C-nucleosides, Sonogashira reaction of ethynyldeoxyriboside with halogenated pyrimidine or pyridine derivatives could be improved by the use of an HMDS-DMF mixed solvent. In situ protection of hydroxy and amino groups by the solvent system may play an important role for the improvement.",

author = "Masahiko Inouye and Yasuhiro Doi and Junichi Azuchi and Wataru Shirato and Junya Chiba and Hajime Abe",

year = "2010",

month = feb,

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doi = "10.3987/COM-10-S(E)89",

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T1 - Hexamethyldisilazane-promoted sonogashira reaction of polyfunctionalized N-containing heterocycles

AU - Inouye, Masahiko

AU - Doi, Yasuhiro

AU - Azuchi, Junichi

AU - Shirato, Wataru

AU - Chiba, Junya

AU - Abe, Hajime

PY - 2010/2/28

Y1 - 2010/2/28

N2 - 1,1,1,3,3,3-Hexamethyldisilazane (HMDS) was found to be an efficient solvent for Sonogashira reaction. For the synthesis of C-nucleosides, Sonogashira reaction of ethynyldeoxyriboside with halogenated pyrimidine or pyridine derivatives could be improved by the use of an HMDS-DMF mixed solvent. In situ protection of hydroxy and amino groups by the solvent system may play an important role for the improvement.

AB - 1,1,1,3,3,3-Hexamethyldisilazane (HMDS) was found to be an efficient solvent for Sonogashira reaction. For the synthesis of C-nucleosides, Sonogashira reaction of ethynyldeoxyriboside with halogenated pyrimidine or pyridine derivatives could be improved by the use of an HMDS-DMF mixed solvent. In situ protection of hydroxy and amino groups by the solvent system may play an important role for the improvement.

UR - http://www.scopus.com/inward/record.url?scp=79952766418&partnerID=8YFLogxK

U2 - 10.3987/COM-10-S(E)89

DO - 10.3987/COM-10-S(E)89

M3 - 学術論文

AN - SCOPUS:79952766418

SN - 0385-5414

VL - 82

SP - 1137

EP - 1141

JO - Heterocycles

JF - Heterocycles

IS - 2

ER -

Hexamethyldisilazane-promoted sonogashira reaction of polyfunctionalized N-containing heterocycles

Abstract

ASJC Scopus subject areas

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