Synthesis 2015; 47(16): 2473-2484
DOI: 10.1055/s-0034-1380656
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis, Rearrangement, and Hauser Annulation of 3-Isocyanophthalides

Dipakranjan Mal*
Department of Chemistry, Indian Institute of Technology, Kharagpur, 721302, India   Email: dmal@chem.iitkgp.ernet.in
,
Ketaki Ghosh
Department of Chemistry, Indian Institute of Technology, Kharagpur, 721302, India   Email: dmal@chem.iitkgp.ernet.in
,
Soumen Chakraborty
Department of Chemistry, Indian Institute of Technology, Kharagpur, 721302, India   Email: dmal@chem.iitkgp.ernet.in
› Author Affiliations
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.

Supporting Information

 
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