26946-72-5Relevant academic research and scientific papers
Environment-friendly and efficient synthesis of 2-aminobenzo-xazoles and 2-aminobenzothiazoles catalyzed by: Vitreoscilla hemoglobin incorporating a cobalt porphyrin cofactor
Li, Fengxi,Li, Zhengqiang,Su, Jiali,Wang, Chunyu,Wang, Ciduo,Wang, Lei,Xu, Yaning,Zhao, Nan
, p. 8047 - 8052 (2021/11/01)
In this study, an environment-friendly and efficient artificial Vitreoscilla hemoglobin (VHb) for the synthesis of 2-aminobenzoxazoles and 2-aminobenzothiazoles has been reported. We demonstrate an expression-based porphyrin substitution strategy to produce VHb containing cobalt porphyrin instead of native hemin, which can catalyze the oxidative cyclization of corresponding 2-aminobenzoxazoles and 2-aminobenthiazoles with up to 97% yield and 4850 catalytic turnovers in water under aerobic conditions. Hence, we provide a green and mild method for the synthesis of 2-aminobenzoxazoles and 2-aminobenzothiazoles. In addition, we indicate the value of porphyrin ligand substitution as a strategy to tune and enhance the catalytic properties of hemoproteins in non-natural reactions.
Electrochemical NaI/NaCl-mediated one-pot synthesis of 2-aminobenzoxazoles in aqueous mediaviatandem addition-cyclization
Huynh, Thao Nguyen Thanh,Koguchi, Shinichi,Rerkrachaneekorn, Tanawat,Sukwattanasinitt, Mongkol,Tankam, Theeranon,Wacharasindhu, Sumrit
supporting information, p. 5189 - 5194 (2021/07/29)
An electrochemical synthesis of 2-aminobenzoxazoles from 2-aminophenols and isothiocyanates was successfully developed in a one-pot fashion. Using inexpensive and widely available NaI and NaCl co-operatively in catalytic amounts, our electrosynthesis approach provided various 2-aminobenzoxazole products in moderate to high yields in an open-flask type undivided cell without using any external supporting electrolyte and base. The protocol can be applied to the synthesis of 2-aminobenzothiazoles from the corresponding 2-thiophenols in moderate yields. This protocol has many benefits. It is metal-free and highly scalable and uses inexpensive mediators and EtOH/water as an environmentally friendly solvent under mild conditions.
Application of cuprous complex containing ortho-position carborane Schiff base ligand
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Paragraph 0057-0061; 0063, (2020/07/21)
The invention relates to an application of a cuprous complex containing an ortho-position carborane Schiff base ligand, and a structural formula of the cuprous complex is shown in the specification, in the formula, Ar is aryl containing a benzene ring or heterocyclic aryl, and . is a boron hydrogen bond; the cuprous complex is used for catalyzing an oxidative coupling reaction of benzoxazole and amine compounds to synthesize 2-amino benzoxazole derivatives. The preparation method specifically comprises the following steps: dissolving a cuprous complex, benzoxazole and an amine compound in an organic solvent, then reacting with an oxidant at 50-80 DEG C for 6-12 hours, and separating and purifying to obtain the 2-amino benzoxazole derivative. Compared with the prior art, the cuprous complexcontaining the ortho-carborane Schiff base ligand can efficiently catalyze oxidative coupling of benzoxazole and primary amine or secondary amine to synthesize the 2-amino benzoxazole derivative; theproduct has the advantages of good selectivity, low catalyst dosage, mild reaction conditions, high reaction rate, high yield, wide substrate range and the like, and shows a wide industrial application prospect.
A Cu2O/TBAB-promoted approach to synthesize heteroaromatic 2-Amines: Via one-pot cyclization of aryl isothiocyanates with ortho-substituted amines in water
Chen, Ling,Dong, Yibo,Wu, Yangjie,Yang, Jinchen,Zhang, Jinli
supporting information, p. 7425 - 7430 (2020/10/13)
An efficient approach to synthesize heteroaromatic 2-Amines from one-pot desulfurization/dehydrogenative cyclization of aryl isothiocyanates with ortho-substituted amines in water was developed. This approach tolerated a wide range of functional groups on
Potassium Periodate Mediated Oxidative Cyclodesulfurization toward Benzofused Nitrogen Heterocycles
Duangkamol, Chuthamat,Pattarawarapan, Mookda,Phakhodee, Wong
, p. 1981 - 1990 (2020/07/03)
A convenient oxidative cyclodesulfurization method toward the synthesis of benzofused nitrogen heterocycles using inexpensive and readily available potassium periodate as an oxidant was developed. Upon treating isothiocyanates with ortho -substituted anilines bearing N, N -, N, O -, and N, S -bis-nucleophiles, followed by an intramolecular cyclization of the in situ generated monothioureas, substituted 2-aminobenzazole series were rapidly accessible in good to excellent yields. The protocol can accommodate various substituents on both substrates while allowing more efficient, greener, and operational simpler process relative to other oxidative coupling reactions. Tetracyclic quinazolinone derivatives were also afforded in high yields in a single preparative step and chromatography-free.
One-pot reaction for the synthesis of N-substituted 2-aminobenzoxazoles using triphenylbismuth dichloride as cyclodesulfurization reagent
Murata, Yuki,Matsumoto, Natsuho,Miyata, Maya,Kitamura, Yuki,Kakusawa, Naoki,Matsumura, Mio,Yasuike, Shuji
, p. 18 - 23 (2018/02/09)
The treatment of various 2-aminophenols with isothiocyanates afforded thioureas, which were reacted in situ with triphenylbismuth dichloride in the presence of triethylamine to give the expected N-substituted benzoxazol-2-amines in good to excellent yields. Triphenylbismuth dichloride promoted the successful cyclodesulfurization of thioureas with short reaction times under mild reaction conditions. This reaction is the first example of the synthesis of heterocyclic rings using a pentavalent organobismuth reagent.
A new NBS/oxone promoted one pot cascade synthesis of 2-aminobenzimidazoles/2-aminobenzoxazoles: A facile approach
Daswani, Ujla,Dubey, Nitin,Sharma, Pratibha,Kumar, Ashok
supporting information, p. 8093 - 8099 (2016/09/12)
A new strategy for the synthesis of 2-aminobenzimidazoles via a reaction of α-halogenated cyclohexanone with guanidine is reported. It provides a facile N-bromosuccinimide (NBS) mediated transition metal free, sustainable path for the synthesis of 2-substituted azoles. NBS along with the oxone promotes in situ halogenation of cyclohexanone, which in turn, when allowed to react with guanidine, afforded 2-aminobenzimidazoles (2-ABI). This eco-friendly protocol provides a competent laboratory synthesis method associated with significant advantages such as greater selectivity, cost-efficiency, mild reaction conditions, absence of chromatographic purification, clean reaction profile, and a simple work-up procedure to furnish high yields. The structures of all the synthesized compounds were confirmed on the basis of IR, 1H and 13C NMR, mass spectrometry, and elemental analyses data. In addition, we have also extended the scope of this strategy for obtaining 2-amino substituted benzoxazoles.
Ultrasound-assisted synthesis of substituted 2-aminobenzimidazoles, 2-aminobenzoxazoles, and related heterocycles
Phakhodee, Wong,Duangkamol, Chuthamat,Wiriya, Nittaya,Pattarawarapan, Mookda
, p. 5290 - 5293 (2016/11/11)
A sonochemical method for the synthesis of 2-aminobenzimidazoles and 2-aminobenzoxazoles, as well as chiral aminooxazolines and a chiral substituted quinazolin-5-one is reported. Using the Ph3P–I2system in the presence of triethylami
Visible-light-promoted cyclodesulfurization of phenolic thioureas: An organophotoredox catalytic approach to 2-aminobenzoxazoles
Yadav, Vinod K.,Srivastava, Vishnu P.,Yadav, Lal Dhar S.
, p. 155 - 158 (2015/12/24)
A facile and efficient one-pot operation for the photo-oxidative cyclodesulfurization of o-phenolic thioureas to afford 2-aminobenzoxazoles is reported. The protocol could be executed under visible light irradiation employing eosin Y as an organophotoredo
Dithiocarbamate promoted practical synthesis of N-Aryl-2-aminobenzazoles: Synthesis of novel Aurora-A kinase inhibitor
Katari, Naresh Kumar,Venkatanarayana,Srinivas, Kummari
, p. 447 - 453 (2015/05/20)
Various N-aryl-2-aminobenzoxazoles and N-aryl-2-aminobenzothiazoles were synthesized from o-aminophenol and o-aminothiophenol, respectively, mediated by dithiocarbamate in one step. The salient features of this method include mild reaction condition, high
