7463-56-1Relevant academic research and scientific papers
Dual Reactivity of 1,2,3,4-Tetrazole: Manganese-Catalyzed Click Reaction and Denitrogenative Annulation
Chattopadhyay, Buddhadeb,Das, Sandip Kumar,Khatua, Hillol,Roy, Satyajit
supporting information, p. 304 - 312 (2020/10/29)
A general catalytic method using a Mn-porphyrin-based catalytic system is reported that enables two different reactions (click reaction and denitrogenative annulation) and affords two different classes of nitrogen heterocycles, 1,5-disubstituted 1,2,3-triazoles (with a pyridyl motif) and 1,2,4-triazolo-pyridines. Mechanistic investigations suggest that although the click reaction likely proceeds through an ionic mechanism, which is different from the traditional click reaction, the denitrogenative annulation reaction likely proceeds via an electrophilic metallonitrene intermediate rather than a metalloradical intermediate. Collectively, this method is highly efficient and offers several advantages over other methods. For example, this method excludes a multi-step synthesis of the N-heterocyclic molecules described and produces only environmentally benign N2 gas a by-product.
Iron-Catalyzed Amination of Strong Aliphatic C(sp3)-H Bonds
Das, Sandip Kumar,Roy, Satyajit,Khatua, Hillol,Chattopadhyay, Buddhadeb
supporting information, p. 16211 - 16217 (2020/10/26)
A concept for intramolecular denitrogenative C(sp3)-H amination of 1,2,3,4-tetrazoles bearing unactivated primary, secondary, and tertiary C-H bonds is discovered. This catalytic amination follows an unprecedented metalloradical activation mechanism. The utility of the method is showcased with the short synthesis of a bioactive molecule. Moreover, an initial effort has been embarked on for the enantioselective C(sp3)-H amination through the catalyst design. Collectively, this study underlines the development of C(sp3)-H bond functionalization chemistry that should find wide application in the context of drug discovery and natural product synthesis.
Pyridine-phosphinimine ligand-accelerated Cu(I)-catalyzed azide-alkyne cycloaddition for preparation of 1-(pyridin-2-yl)-1,2,3-triazole derivatives
Sun, Ranfeng,Wang, Huangdong,Hu, Jianfeng,Zhao, Jiudong,Zhang, Hao
, p. 5954 - 5963 (2014/08/05)
A series of phosphinimine ligands were designed and used in the Cu(i)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction of tetrazolo[1,5-a]pyridines and alkynes for the first time. By optimizing the reaction conditions, an efficient catalytic system (CuCl/2-PyCH 2NPtBu3) was developed to give 1-(pyridin-2-yl)-1,2,3-triazole derivatives in moderate to excellent yields (46-98%). This journal is the Partner Organisations 2014.
Application of the intramolecular aza-Wittig reaction to the synthesis of pyrido[2,3-d]pyrimidines
Chan, Johann,Faul, Margaret
, p. 3361 - 3363 (2007/10/03)
Pyrido[2,3-d]pyrimidines are synthesized in a two-step procedure from amides and tetrazolo[1,5-a]pyridine-8-carbonyl chloride. Reaction of the crude imides with triphenylphosphine effects an intramolecular aza-Wittig reaction to afford a variety of substi
