248-01-1Relevant academic research and scientific papers
Copper-catalyzed C-H azidation of anilines under mild conditions
Tang, Conghui,Jiao, Ning
supporting information, p. 18924 - 18927 (2013/01/15)
A novel and efficient copper-catalyzed azidation reaction of anilines via C-H activation has been developed. This method, in which the primary amine acts as a directing group by coordinating to the metal center, provides ortho azidation products regioselectively under mild conditions. This effective route for the synthesis of aryl azides is of great significance in view of the versatile reactivity of the azide products.
An intramolecular [2 + 3] cycloaddition route to fused 5-heterosubstituted tetrazoles
Demko, Zachary P.,Sharpless, K. Barry
, p. 4091 - 4094 (2007/10/03)
(matrix presented) Fused 5-heterotetrazole ring systems are synthesized in high yield via intramolecular [2 + 3] cycloadditions of organic azides and heteroatom-substituted nitriles. Cyanates, thiocyanates, and cyanamides are all competent dipolarophiles for this reaction. A variety of scaffolds are tolerated when the new enclosed ring is five- or six-membered.
Studies on Heterocyclic Compounds. Part VI: Synthesis of Bridgehead Nitrogen Triazine and Pyrimidine Heterocycles
Dehuri, S. N.,Pradhan, P. C.,Nayak, A.
, p. 475 - 478 (2007/10/02)
New bridgehead nitrogen containing heterocycles such as thiazolotriazine (IVa and IVb), imidazolotriazine (IVc), triazinotriazine (IVd and IVe) and oxadiazolotriazine (IVf) and several of their derivatives (V) have been prepared by reacting their respective hydrazine (II) with ethylpyruvate and phenyl glycoxalic acid.The diazotization of hydrazine (II) furnished the reactive intermediates (VI) (azido form) and (VII) (tetrazole form) depending on the structure of hydrazines.These intermediates have been used to synthesise bridgehead nitrogen pyrimidine derivatives (VIII) by reacting them with diethyl fumarate.The spectral and chemical evidences show that diazotised products obtained from 2-hydrazino-4-phenyl thiazole (IIa) and 2-hydrazino benzothiazole (IIb) exist in tetrazole form (VIIa) and (VIIb), respectively, whereas the remaining four (IIa-IIf) remain in the azido form (VIc-VIf) in the solid state.
