5577-04-8Relevant academic research and scientific papers
One-pot synthesis of multisubstituted benzimidazoles via sequential Ugi and catalytic aza-wittig reaction starting from 2-aminobenzoyl azides
Yan, Yan-Mei,Rao, Yong,Ding, Ming-Wu
, p. 1263 - 1268 (2016)
A simple and one-pot synthesis of multisubstituted benzimidazoles by a Ugi 4CC/catalytic aza-Wittig sequence was developed. The reaction of 2-aminobenzoyl azide 2, aldehyde 3, acid 4, and isocyanide 5 produced the benzimidazoles 8 in moderate to good yields via a sequential Ugi condensation and catalytic aza-Wittig in the presence of a catalytic amount of phospholene oxide.
Nitrosation with Sodium Hexanitrocobaltate(III)
Stefane, Bogdan,Kocevar, Marijan,Polanc, Slovenko
, p. 7165 - 7169 (2007/10/03)
Na3Co(NO2)6 has been investigated as a new reagent for the nitrosation of various substrates containing an amino functionality. Reactions took place in an aqueous solution of the reagent. The pH of the reaction mixture remained in the range 4.3-5. Thus, hydrazides were transformed to the corresponding acyl azides, and the reactions with arenesulfonyl hydrazines afforded arenesulfonyl azides. Treatment of aromatic amines with Na3Co(NO2)6 gave 1,3-diaryltriazenes in excellent yields; coupling of the initially formed diazo compound to the electron rich aromatic ring was also observed. Nitrosation of aliphatic amines was not possible due to complex formation with the reagent.
Schmidt reaction of some constrained aromatic acids, and related topics
Ruediger, Edward H.,Gandhi, Sham S.,Gibson, Martin S.,Farcasiu, Dan,Uncuta, Cornelia
, p. 577 - 579 (2007/10/02)
Schmidt reaction of phthalic acid in 90-98percent sulfuric acid gives anthranilic acid and anthranilazide (major products) by a process considered to involve 3,1-benzoxazin-2,4(1H)-dione as intermediate.Benzimidazol-2-one is produced in this reaction by a secondary process from anthranilazide; it is also produced by photolysis of anthranilazide.Under Schmidt reaction conditions, 1,2,3-benzotriazin-4(3H)-one gives o-azidobenzamide.Under similar conditions, the lactol of 4-formyl-5-phenanthroic acid gives 1-azapyren-2(1H)-one and phenanthrene-4,5-dicarboximide, while phenanthrene-4,5-dicarboxylic acid gives 1-azapyren-2(1H)-one.Diphenic acid yields phenanthridone and 2,2'-diaminobiphenyl in proportions dependent on the sulfuric acid concentration.
