Electrophilic cyclization of N-allyl(propargyl)-5-amino-1H-pyrazole-4-carboxamides. Synthesis of 4-[(dihydro)oxazol-2-yl]-1H-pyrazol-5-amines View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2015-12

AUTHORS

N. A. Bondarenko, A. I. Vas’kevich, A. V. Bol’but, E. B. Rusanov, M. V. Vovk

ABSTRACT

N-Allyl-5-amino-1H-pyrazole-4-carboxamides in reactions with polyphosphoric acid, with N-halosuccinimides in chloroform, and with (chlorosulfanyl)benzenes in nitromethane in the presence of lithium perchlorate underwent cyclization involving the N-allylamide fragment to give 4-[5-methyl(halomethyl)-4,5-dihydrooxazol-2-yl]-1H-pyrazol-5-amines and 2-(5-amino-1H-pyrazol-4-yl)-5-[(arylsulfanyl)methyl]-4,5-dihydro-1,3-oxazolium perchlorates, respectively. Analogous reactions of N-propargyl-5-amino-1H-pyrazole-4-carboxamides with polyphosphoric acid afforded 4-(5-methyloxazol-2-yl)-1H-pyrazol-5-amines, and with (chlorosulfanyl) benzenes, 2-(5-amino-1H-pyrazol-4-yl)-5-[(arylsulfanyl)methylidene]-4,5-dihydro-1,3-oxazolium perchlorates.

PAGES

1774-1783

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s1070428015120209

DOI

http://dx.doi.org/10.1134/s1070428015120209

DIMENSIONS

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