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Synthesis 2015; 47(16): 2473-2484
DOI: 10.1055/s-0034-1380656
DOI: 10.1055/s-0034-1380656
paper
Synthesis, Rearrangement, and Hauser Annulation of 3-Isocyanophthalides
Further Information
Publication History
Received: 27 January 2015
Accepted after revision: 27 March 2015
Publication Date:
19 May 2015 (online)
Abstract
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.
Key words
3-isocyanoisobenzofuran-1(3H)-ones - synthesis - Hauser annulations - rearrangement - 3-cyanoisobenzofuran-1(3H)-onesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380656.
- Supporting Information
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