One-Pot Synthesis of Spiro-isobenzofuran Compounds via the Sequential Condensation/Oxidation Reaction of Ninhydrin with 4-Amino-1,2-naphthoquinones/2-Amino-1,4-naphthoquinones under Mild Conditions

Seyedeh Hekmat Mousavi; Mohammad Reza Mohammadizadeh; Zohreh Roshan; Azar Jamaleddini; Satoru Arimitsu

doi:10.1021/acsomega.0c01934

One-Pot Synthesis of Spiro-isobenzofuran Compounds via the Sequential Condensation/Oxidation Reaction of Ninhydrin with 4-Amino-1,2-naphthoquinones/2-Amino-1,4-naphthoquinones under Mild Conditions

ACS Omega. 2020 Jul 19;5(29):18273-18288. doi: 10.1021/acsomega.0c01934. eCollection 2020 Jul 28.

Authors

Seyedeh Hekmat Mousavi¹, Mohammad Reza Mohammadizadeh^{1

2}, Zohreh Roshan¹, Azar Jamaleddini¹, Satoru Arimitsu³

Affiliations

¹ Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr 75169, Iran.
² Oil and Gas Research Center, Persian Gulf University, Bushehr 75169, Iran.
³ Department of Chemistry, Biology and Marine Science, University of the Ryukyus, Senbaru 1, Nakagami, Nishihara, Okinawa 903-0213, Japan.

Abstract

A one-pot route for the synthesis of spiro-isobenzofuran compounds was developed via the condensation reaction of ninhydrin with 4-amino-1,2-naphthoquinones or 2-amino-1,4-naphthoquinones in acetic acid followed by the oxidative cleavage of the corresponding vicinal diols at room temperature. Various derivatives of spiro[benzo[g]indole-2,1'-isobenzofuran]-3,3',4,5(1H) tetraones and spiro[benzo[f]pyrrolo[2,3-h]quinoxaline-2,1'-isobenzofuran]-3,3'(1H)-diones were synthesized in good to high yields. Moreover, further condensation of spiro[benzo[g]indole-2,1'-isobenzofuran]-3,3',4,5(1H)-tetraones with 1,2-diamines resulted in the new spiro-isobenzofuran compounds having phenazine rings in high yields.