29644-82-4Relevant articles and documents
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Raiford,Linsk
, p. 879 (1945)
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Oxidative NHC Catalysis for the Generation of Imidoyl Azoliums: Synthesis of Benzoxazoles
Patra, Atanu,James, Anjima,Das, Tamal Kanti,Biju, Akkattu T.
, p. 14820 - 14826 (2019/01/03)
N-Heterocyclic carbene (NHC)-catalyzed intramolecular cyclization of aldimines generated from 2-amino phenols and aromatic aldehydes leading to the synthesis of 2-arylbenzoxazoles under mild conditions is presented. The reaction proceeds via the generation of the aza-Breslow intermediates from imines and NHC, which under oxidative conditions form the key imidoyl azoliums and a subsequent intramolecular cyclization furnishes the product. The reaction tolerates a broad range of functional groups, and the products are formed in generally good yields.
Cyanide as a powerful catalyst for facile synthesis of benzofused heteroaromatic compounds via aerobic oxidation
Cho, Yeon-Ho,Lee, Chun-Young,Cheon, Cheol-Hong
, p. 6565 - 6573 (2013/07/26)
Highly efficient synthesis of benzofused heteroaromatic compounds via aerobic oxidation catalyzed by cyanide anion has been developed. The Schiff bases derived from 2-aminophenol and aldehydes provided the corresponding benzoxazoles in high yields in the presence of a catalytic amount of cyanide in an open flask under ambient conditions without the use of any external metal co-oxidants and bases. Furthermore, we have developed a catalytic sequential one-step protocol for the synthesis of benzoxazoles by adding a catalytic amount of NaCN to Schiff bases generated in situ from 2-aminophenol and aldehydes without the isolation of imine intermediates. This one-pot protocol was further extended to the synthesis of benzothiazoles from 2-aminothiophenol and aldehydes. A variety of aldehydes could be applied to this sequential one-pot protocol and the desired benzofused azole products were obtained in high yields.