78749-89-0Relevant academic research and scientific papers
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
Copper-catalyzed direct amination of benzoxazoles using primary amines as nitrogen sources
Gu, Jian,Cai, Chun
supporting information, p. 639 - 642 (2015/03/14)
A facile, efficient, and simple protocol for direct oxidative C-H amination of benzoxazoles with primary amines through copper-catalyzed C-H bond activation using tert-butyl peroxide (TBP) as oxidant under air has been developed. The reaction proceeds smoothly at ambient temperature to furnish the products. A variety of substituted aminobenzoxazoles were synthesized with good to excellent yields.
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).
An economically and environmentally sustainable synthesis of 2-aminobenzothiazoles and 2-aminobenzoxazoles promoted by water
Zhang, Xinying,Jia, Xuefei,Wang, Jianji,Fan, Xuesen
supporting information; experimental part, p. 413 - 418 (2011/04/16)
Tandem reactions of isothiocyanates (1) with 2-aminothiophenols (2), or isothiocyanates (1) with 2-aminophenols (4), were carried out rapidly and efficiently in water. A significant rate acceleration of the reaction between 1a and 2a in water compared wit
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.
A New Method for the Preparation of 2-(Alkylamino)benzoxazoles and 2-(Alkylimino)benzoxazolines
Yamato, Masatoshi,Takeuchi, Yasuo,Hattori, Kyoko,Hashigaki, Kuniko
, p. 3053 - 3060 (2007/10/02)
New syntheses of 2-(alkylamino)benzoxazoles (III) and 3-alkyl-2-(alkylimino)benzoxazolines (IV) were developed.Various compounds III were obtained by the reaction of 2-(methylthio)benzoxazole with amines.In the alkylation of 2-(monoalkylamino)benzoxazoles, the use of a base as a catalyst was found to be important for the selective preparation of 2-(N,N-dialkylamino)benzoxazoles; in the absence of base, IV was obtained.On the other hand, alkylation of N,N'-dialkyl-N-(2-hydroxyphenyl)thioureas resulted in the development of another method for the preparation of IV.Keywords - 2-(alkylamino)benzoxazole; 3-alkyl-2-(alkylimino)benzoxazoline; 2-(methylthio)benzoxazole; N,N'-dialkyl-N-(2-hydroxyphenyl)thiourea; 3-alkylbenzoxazoline-2-thione
SYNTHESIS AND IR SPECTRA OF SOME 2-AMINOBENZOXAZOLE DERIVATIVES
Simov, D.,Davidkov, K.
, p. 437 - 440 (2007/10/02)
A large number of 5-nitro-, 6-nitro-, 5-chloro-, and 6-bromo-2-aminobenzoxazoles were synthesized by the reaction of benzoxazoline-2-thiones with various amines.It was shown by IR spectroscopy that all of the compounds exist in the amino form in solution,
