1,3-Dipolar cycloaddition of azinium ylides to alkynyl hetarenes: a synthetic route to indolizine and pyrrolo[2,1-a]isoquinoline based heterobiaryls
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- 作者：Julia I. Nelina-Nemtsevaa ; Anna V. Gulevskayaa ; agulevskaya@sfedu.ru" class="auth_mail" title="E-mail the corresponding author ; anvasgul@gmail.com" class="auth_mail" title="E-mail the corresponding author ; Alexander F. Pozharskiia ; Huong T.L. Nguyenb ; Ekaterina A. Filatovaa
- 关键词：1 ; 3-Dipolar cycloaddition ; Azinium ylides ; Alkynyl hetarenes ; Indolizines ; Pyrrolo[2 ; 1-a]isoquinolines ; Heterobiaryls
- 刊名：Tetrahedron
- 出版年：2016
- 出版时间：5 May 2016
- 年：2016
- 卷：72
- 期：18
- 页码：2327-2335
- 全文大小：1298 K
文摘
For the first time, π-deficient alkynyl hetarenes were used as dipolarophiles in a 1,3-dipolar cycloaddition reaction with in situ generated azinium ylides. A three-component reaction of pyridine or isoquinoline, ethyl chloroacetate and alkynyl hetarene (pyrazine, quinoxaline, uracil, or lumazine derivative) in the presence of a base gave the corresponding indolizine or pyrrolo[2,1-a]isoquinoline based heterobiaryl in good yields. The reactions proceeded with high regioselectivity; in all cases the most electron-deficient carbon atom of the C
class="glyphImg imgLazyJSB">C bond of the starting alkynyl hetarene adds to the side-chain carbon of the azinium ylide. 1,3-Dipolar cycloaddition reactions of alkynyl hetarenes with azinium ylides or other 1,3-dipole reagents can be considered as an alternative synthetic approach to heterobiaryls.
class="glyphImg imgLazyJSB">C bond of the starting alkynyl hetarene adds to the side-chain carbon of the azinium ylide. 1,3-Dipolar cycloaddition reactions of alkynyl hetarenes with azinium ylides or other 1,3-dipole reagents can be considered as an alternative synthetic approach to heterobiaryls.