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An efficient two‐step synthesis of novel thiazolo[2,3‐ b ]pyrazolo[3,4‐ f ][1,3,5]triazepines
Author(s) -
Insuasty Braulio,
Tigreros Alexis,
Martínez Henry,
Quiroga Jairo,
Abonia Rodrigo,
Gutierrez Alexander,
Nogueras Manuel,
Cobo Justo
Publication year - 2009
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.145
Subject(s) - chemistry , rhodanine , dimethylformamide , mass spectrometry , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , chromatography , solvent
AbstractIn an attempt to carry out a straightforward synthesis of thiazolopyrazolodiazepines from the reaction of 4,5‐diamino‐3‐methyl‐1‐phenylpyrazole 1 with arylidene derivatives of rhodanine 2 , the unplanned (Z) ‐ 2′‐[(5‐amino‐3‐methyl‐1‐phenylpyrazol‐4‐yl)imino]‐5‐arylidenethiazolidin‐4‐ones 4 were obtained as unique products. Nevertheless, the treatment of these compounds with aliphatic aldehydes in dimethylformamide provided the novel thiazolo[2,3‐ b ]pyrazolo[3,4‐ f ][1,3,5]triazepines 5 and 6 in good to excellent yields. All the structures of the obtained compounds were assigned on the basis of IR, 1D and 2D NMR measurements, mass spectrometry, and microanalysis. J. Heterocyclic Chem., (2009).