78749-89-0Relevant articles and documents
Microwave-assisted hydrogen peroxide-mediated synthesis of benzoxazoles and related heterocycles via cyclodesulfurization
Kadagathur, Manasa,Sigalapalli, Dilep Kumar,Patra, Sandip,Tangellamudi, Neelima D.
supporting information, p. 2213 - 2224 (2021/05/26)
A novel approach has been developed to construct benzoxazoles and similar N- and S-containing heterocycles from their corresponding isothiocyanates and o-substituted anilines via cyclodesulfurization. The reaction was found to proceed via in situ formatio
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).
A mild and efficient one-pot synthesis of 2-aminated benzoxazoles and benzothiazoles
Stewart, Gavin W.,Baxter, Carl A.,Cleator, Ed,Sheen, Faye J.
supporting information; experimental part, p. 3229 - 3231 (2009/08/15)
Previous syntheses of the biologically active 2-aminated benzoxazoles have relied on forcing thermal conditions to generate the products directly from the corresponding thiols. The resulting yields have ranged from moderate to poor. A mild and high-yielding alternative one-pot chlorination-amination procedure is described. Compounds with a variety of substitution patterns are reported and the methodology has been successfully extended to benzothiazoles. Palladium catalysis on suitably activated examples has been employed to generate the desired compounds of interest.