Synthesis of NH-, 2H-4,5-Dihydrobenz[g]inazoles and Related Compounds from 1-Tetralone Carbomethoxyhydrazones and Aromatic Esters
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- 作者：John D. Knight ; Catherine R. Kramp ; Ebony J. Hilton ; Jarrett H. Vella ; Bonnie J. Grant ; Laela M. Hajiaghamohseni ; Michelle A. Meierhoefer ; S. Patrick Dunn ; Matthew J. Walters ; Jason S. Overby ; Clyde R
- 刊名：Industrial & Engineering Chemistry Research
- 出版年：2007
- 出版时间：December 19, 2007
- 年：2007
- 卷：46
- 期：26
- 页码：8959 - 8967
- 全文大小：155K
- 年卷期：v.46,no.26(December 19, 2007)
- ISSN：1520-5045
文摘
The carbomethoxhydrazones of 1-tetralone, 6-methoxy-1-tetralone, and 5,7-dimethyl-1-tetralone were convertedto dilithiated intermediates with excess lithium diisopropylamide and condensed with aromatic esters to giveC-acylated intermediates that were not usually isolated but cyclized directly with acid to afford theN-carbomethoxydihydrobenzindazoles. These compounds could be separately saponified followed bydecarboxylation to the targeted NH-dihydrobenzindazoles. Single-crystal X-ray analysis for several compoundsindicated that a single tautomer was present, with the NH-hydrogen atom bonded exclusively to the N-2 ofthe products. Theoretical calculations indicated this product to be the more stable of the two tautomers.