84312-15-2Relevant articles and documents
Synthesis of N,N'-Diacylindigotins (N,N'-Diacyl-2,2'-bi-indolinylidene-3,3'-diones) via an Oxidative Oxygen-to-Nitrogen Acyl Shift of O,O'-Diacyl-leucoingigos(3,3'-Diacyloxy-2,2'-bi-indolyls)
Setsune, Jun-ichiro,Wakemoto, Hirofumi,Matsueda, Taizo,Matsuura, Toshikazu,Tajima, Hideaki,et al.
, p. 2305 - 2310 (2007/10/02)
O,O'-Diacyl-leucoindigos (3f-j), which were readily obtained by the reaction of leucoindigo disodium salt (4) with acyl chlorides, underwent rapid oxidation by 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) to fenerate the indigo chromophore with concomitant shift of the acyl groups intramolecularly from oxygen to nitrogen.A number of N,N'-diacylindigotins with functionalized acyl groups were prepared by this method and the direct N-acylation method .A large bathochromic shift of the visible absorption band in the cis form of N,N'-diacylindigotins with bulky acyl groups (2c), (2d), and (2j) was observed which suggested that the electronic structure of the indigo chromophore is perturbed by the steric constraint of the N-acyl groups.
Synthesis and cis-to-trans Isomerization of N,N'-Diacyl Derivatives of Indigotion
Setsune, Jun-ichiro,Wakemoto, Hirofumi,Matsukawa, Kimihiro,Ishihara, Sho-ichi,Yamamoto, Ryo-ichi,Kitao, Teijiro
, p. 1022 - 1023 (2007/10/02)
The oxidative rearrangement of O,O'-diacyl derivatives of leucoindigo with dichlorodicyanobenzoquinone in dimethyl sulfoxide affords N,N'-diacyl derivatives of indigotin in high yield; it has been found that the heat of cis-to-trans isomerization in aceto
