- Synthesis of Structurally Diverse Benzotriazoles via Rapid Diazotization and Intramolecular Cyclization of 1,2-Aryldiamines
-
An operationally simple method has been developed for the preparation of N-unsubstituted benzotriazoles by diazotization and intramolecular cyclization of a wide range of 1,2-aryldiamines under mild conditions, using a polymer-supported nitrite reagent and p-tosic acid. The functional group tolerance of this approach was further demonstrated with effective activation and cyclization of N-alkyl, -aryl, and -acyl ortho-aminoanilines leading to the synthesis of N1-substituted benzotriazoles. The synthetic utility of this one-pot heterocyclization process was exemplified with the preparation of a number of biologically and medicinally important benzotriazole scaffolds, including an α-amino acid analogue.
- Faggyas, Réka J.,Sloan, Nikki L.,Buijs, Ned,Sutherland, Andrew
-
p. 5344 - 5353
(2019/05/21)
-
- PROCESS FOR THE PREPARATION OF ε-ALKOXYCARBONYLLYSINES AND THEIR ANALOGUES
-
A process for the preparation of ω-alkoxycarbonylamino-α-aminoacids and α,ω orthogonally diprotected diaminoacids from α,ω-diaminoacids using 1- alkoxycarbonylbenzotriazoles as protecting agents is disclosed. In an alternative embodiment, carbamoylating agents in the presence of benzotriazoles are used instead of 1-alkoxycarbonylbenzotriazoles. This reaction is preferably applied to the preparation of ε- alkoxycarbonyllysines from lysine. A process for the preparation of t-butoxycarbonylbenzotriazoles and novel complexes of ω-alkoxycarbonylamino-α-aminoacids with benzotriazoles are also disclosed.
- -
-
Page/Page column 16-17
(2008/06/13)
-
- STUDIES ON THE THERMAL DECARBOXYLATION OF 1-ALKOXYCARBONYLBENZOTRIAZOLES
-
1-Alkoxycarbonylbenzotriazoles on thermolysis lose carbon dioxide; the decarboxylation is accompanied by the formation of a mixture of 1- and 2-alkylbenzotriazoles, with the N-1 isomer predominating over the N-2 isomer in all cases.A cross-over experiment
- Katritzky, Alan R.,Zhang, Gui-Fen,Fan, Wei-Qiang,Wu, Jing,Pernak, Juliusz
-
p. 567 - 573
(2007/10/02)
-
- On the Synthesis of Benzyloxycarbonyl Amino Acids
-
Dibenzyl dicarbonate and 1-benzyloxycarbonyl-benzothiazole are proposed as efficient new acyl donors for the introduction of the benzyloxycarbonyl group into amines for the reversible protection of amino functions particularly in peptide synthesis.
- Wuensch, E.,Graf, W.,Keller, O.,Keller, W.,Wersin, G.
-
p. 958 - 960
(2007/10/02)
-