NDLI: Inverse electron-demand 1,3-dipolar cycloaddition of nitrile oxide with common nitriles leading to 3-functionalized 1,2,4-oxadiazoles

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Inverse electron-demand 1,3-dipolar cycloaddition of nitrile oxide with common nitriles leading to 3-functionalized 1,2,4-oxadiazoles

Content Provider	Royal Society of Chemistry (RSC)
Author	Hirao, Shotaro Ariga, Masahiro Nishiwaki, Nagatoshi Ise, Yumiko Kobiro, Kazuya Sawayama, Jun Saigo, Kazuhiko Okajima, Yoshikazu
Copyright Year	2011
Abstract	A carbamoyl-substituted nitrile oxide was generated upon treatment of easily available 2-methyl-4-nitro-3-isoxazolin-5(2H)-one with THF (not dried); the reaction proceeded efficiently even in the absence of any special reagents and reaction conditions. The nitrile oxide caused 1,3-dipolar cycloaddition with common aliphatic nitriles or electron-rich aromatic nitriles to afford 3-functionalized 1,2,4-oxadiazoles, which are expected to serve as precursors for the preparation of a variety of functional materials by the chemical transformation of the carbamoyl group. While conventional preparative methods for 1,2,4-oxadiazoles involve the cycloaddition of an electron-rich nitrile oxide with an electron-deficient nitrile or a nitrile activated by a Lewis acid, our method employs the complementary combination of an electron-rich nitrile and an electron-deficient nitrile oxide- the inverse electron-demand 1,3-cycloaddition. The DFT calculations using B3LYP 6-31G* supported the abovementioned inverse reactivity, and also suggested the presence of an accelerating effect by the carbamoyl group as a result of hydrogen bond formation with a dipolarophilic nitrile.
Starting Page	6750
Ending Page	6754
Page Count	5
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	9
Issue Number	19
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/c1ob05682d
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	1,3-Dipolar cycloaddition Cycloaddition Nitrile Aliphatic compound Carboxylic acid Hydrogen bond
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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