Synthesis, Rearrangement, and Hauser Annulation of 3-Isocyanophthalides

被引：6

作者：

Mal, Dipakranjan ^{[1
]}

Ghosh, Ketaki ^{[1
]}

Chakraborty, Soumen ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kharagpur 721302, W Bengal, India

来源：

SYNTHESIS-STUTTGART | 2015年 / 47卷 / 16期

关键词：

3-isocyanoisobenzofuran-1(3H)-ones; synthesis; Hauser annulations; rearrangement; 3-cyanoisobenzofuran-1(3H)-ones; ISOCYANIDE-CYANIDE REARRANGEMENT; INHIBITOR THYSANONE; EFFICIENT SYNTHESIS; ISONITRILES; DERIVATIVES; 3-CYANO-1(3H)-ISOBENZOFURANONES; ANNELATION; CONVERSION; ANALOG; ROUTE;

D O I：

10.1055/s-0034-1380656

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Isocyanoisobenzofuran-1(3H)-ones (phthalides) were prepared in two steps from the corresponding phthalaldehydic acids. The 3-isocyanoisobenzofuran-1(3H)-ones are readily rearranged to the corresponding 3-cyanoisobenzofuran-1(3H)-ones using triflic anhydride and 2,6-lutidine, thus enabling the synthesis of 3-cyanoisobenzofuran-1(3H)-ones without using toxic cyanide. Furthermore their annulation with Michael acceptors results in direct formation of 1,4-naphthoquinols/1,4-naphthoquinones in moderate yields.

引用

页码：2473 / 2484

页数：12

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