10450-11-0Relevant articles and documents
Organocatalytic Visible Light Enabled SNAr of Heterocyclic Thiols: A Metal-Free Approach to 2-Aminobenzoxazoles and 4-Aminoquinazolines
Rattanangkool, Eakkaphon,Sukwattanasinitt, Mongkol,Wacharasindhu, Sumrit
, p. 13256 - 13262 (2017)
The direct amination reaction of heterocyclic thiols has been developed in the presence of the nonhazardous photocatalyst Rose Bengal under irradiation of visible light. The reaction provides a straightforward approach to pharmaceutically and synthetically useful 2-aminobenzoxazole and 4-aminoquinazoline derivatives from the corresponding heterocyclic thiols with amines in good to excellent yields. Our photochemical reaction can be successfully adapted into a continuous flow reactor which is applicable for large-scale chemical industry. The key benefits of this reaction include the use of metal-free, low-cost Rose Bengal catalyst and practical operation (ambient temperature, open flask, and undried solvents).
A convenient one-pot synthesis of N-substituted 2-aminoazole derivatives
Yotphan, Sirilata,Beukeaw, Danupat,Reutrakul, Vichai
, p. 936 - 942 (2013)
A practical protocol for the one-pot synthesis of N-substituted 2-aminoazole derivatives is described, employing simple azole substrates, nitrogen nucleophiles, lithium tert-butoxide as the base, and iodine to mediate carbon-nitrogen bond formation. This method proceeds at room temperature under an air atmosphere using a normal benchtop set-up, or can be performed conveniently using microwave irradiation. Georg Thieme Verlag Stuttgart - New York.
Microwave-assisted hydrogen peroxide-mediated synthesis of benzoxazoles and related heterocycles via cyclodesulfurization
Kadagathur, Manasa,Sigalapalli, Dilep Kumar,Patra, Sandip,Tangellamudi, Neelima D.
, p. 2213 - 2224 (2021)
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
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.