439133-50-3Relevant academic research and scientific papers
A new and convenient synthesis of 1,2-diamino-3-hetarylpyrrole derivatives
Volovenko, Yulian M.,Tverdokhlebov, Anton V.,Gorulya, Alexandr P.,Shishkina, Svetlana V.,Zubatyuk, Roman I.,Shishkin, Oleg V.
, p. 663 - 668 (2007/10/03)
A number of 1-acylamino-2-amino-3-hetaryl-4-oxo-2-pyrrolines 13-50 were prepared by treatment of 4-chloro-2-hetaryl-3-oxobutanenitriles 11a-h with substituted benzoic and 2-furanoic acid hydrazides in DMF at 110-120°C. When the same reagents were coupled in the presence of triethylamine, a definite dependence of the course of the reaction on the nature of the chloronitriles 11a-h was observed. The steric arrangement of the heterocyclic nitrogen atom in chloronitriles 11 seemed to have a critical influence on the nature of the products obtained. Thus, compounds 11d-h with sterically hindered nitrogen atoms gave the pyrrolines 25-50 mentioned above, while unhindered derivatives 11a-c afforded products of intramolecular alkylation, namely the 3-cyano-2-oxo-1,2-dihydropyrrolo[1,2-a]benzazoles 51-53. An X-ray diffraction study of 2-amino-3-(2-benzothiazolyl)-1-(p-nitrobenzoylamino)-4-oxo-2-pyrroline (24) was carried out to confirm the structures of compounds 13-50 unambiguously. An attempt to extend this reaction to p-tolylsulfonylhydrazine resulted in the simple alkylation products 12a, 12c, and 12e, without subsequent ring closure.
