Synthesis of NH-, 2H-4,5-Dihydrobenz[g]inazoles and Related Compounds from 1-Tetralone Carbomethoxyhydrazones and Aromatic Esters

Autor:	Michelle A. Meierhoefer, Ebony J. Hilton, John D. Knight, Matthew J. Walters, Clyde R. Metz, Jarrett H. Vella, Catherine R. Kramp, S. Patrick Dunn, Charles F. Beam, and Donald G. VanDerveer, Laela M. Hajiaghamohseni, Jason S. Overby, William T. Pennington, Bonnie J. Grant
Rok vydání:	2007
Předmět:	chemistry.chemical_compound chemistry 1-Tetralone Decarboxylation General Chemical Engineering Organic chemistry General Chemistry Lithium diisopropylamide Tautomer Industrial and Manufacturing Engineering Saponification
Zdroj:	Industrial & Engineering Chemistry Research. 46:8959-8967
ISSN:	1520-5045 0888-5885
DOI:	10.1021/ie070760j
Popis:	The carbomethoxhydrazones of 1-tetralone, 6-methoxy-1-tetralone, and 5,7-dimethyl-1-tetralone were converted to dilithiated intermediates with excess lithium diisopropylamide and condensed with aromatic esters to give C-acylated intermediates that were not usually isolated but cyclized directly with acid to afford the N-carbomethoxydihydrobenzindazoles. These compounds could be separately saponified followed by decarboxylation to the targeted NH-dihydrobenzindazoles. Single-crystal X-ray analysis for several compounds indicated that a single tautomer was present, with the NH-hydrogen atom bonded exclusively to the N-2 of the products. Theoretical calculations indicated this product to be the more stable of the two tautomers.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::907450aa13848caa7a4f61a768d3c6ca https://doi.org/10.1021/ie070760j Zobrazit plný text záznamu