100817-80-9Relevant academic research and scientific papers
Diacetoxyiodobenzene assisted C-O bond formation: Via sequential acylation and deacylation process: Synthesis of benzoxazole amides and their mechanistic study by DFT
Nahakpam, Lokendrajit,Chipem, Francis A. S.,Chingakham, Brajakishor S.,Laitonjam, Warjeet S.
supporting information, p. 7735 - 7745 (2016/08/24)
An efficient method for the transformation of N-substituted-N′-benzoylthioureas to substituted N-benzoxazol-2-yl-amides using diacetoxyiodobenzene (DIB) is described in this work. The transformation follows the C-O bond formation leading to the benzoxazole derivative, due to oxidative dehydrogenation by DIB, instead of the expected C-S bond formation of the benzothiazole moiety. The C-O bond formation leading to benzoxazole is due to consecutive acylation and deacylation in conjunction with the reduction of two moles of DIB. A plausible mechanism was proposed for the reaction and density functional calculations were also performed to study the reaction mechanism.
An efficient solid-phase parallel synthesis of 2-amino and 2-amidobenzo[d]oxazole derivatives via cyclization reactions of 2-hydroxyphenylthiourea resin
Jung, Se-Lin,Kim, Seul-Gi,Lee, Gee-Hyung,Gong, Young-Dae
, p. 4109 - 4116 (2013/08/23)
An efficient solid-phase methodology has been developed for the synthesis of 2-amino and 2-amidobenzo[d]- oxazole derivatives. The key step in this procedure involves the preparation of polymer-bound 2-aminobenzo- [d]oxazole resins 4 by cyclization reaction of 2-hydroxyphenylthiourea resin 3. The resin-bound 2-hydroxyphenylthiourea 3 is produced by the addition of 2-aminophenol to the isothiocyanate-terminated resin 2 and serve as a key intermediate for the linker resin. This core skeleton 2-aminobenzo[d]oxazole resin 4 undergoes functionalization reaction with various electrophiles, such as alkylhalides and acid chlorides to generate 2- amino and 2-amidobenzo[d]oxazole resins 5 and 6 respectively. Finally, 2-amino and 2-amidobenzo[d]oxazole derivatives 7 and 8 are then generated in good yields and purities by cleavage of the respective resins 5 and 6 under trifluoroacetic acid (TFA) in dichloromethane (CH2Cl2).
Synthesis of benzoxazole amides as novel antifungal agents against Malassezia furfur
Kim, Beom Joon,Kim, Jinah,Kim, Young-Kook,Choi, Soon-Yong,Choo, Hea-Young Park
experimental part, p. 1270 - 1274 (2010/09/18)
Malassezia is a pathogenic fungus that causes skin diseases, such as tinea versicolor, atopic dermatitis and fatal sepsis. We report the synthesis of a series of benzoxazole amides and evaluation of their antifungal activity against Malassezia furfur. Twe
