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Synthesis and Basicity Studies of Quinolino[7,8- h]quinoline Derivatives

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journal contribution
posted on 24.11.2021, 20:18 by GJ Rowlands, RJ Severinsen, JK Buchanan, Karl ShafferKarl Shaffer, HT Jameson, N Thennakoon, I Leito, M Lõkov, A Kütt, R Vianello, I Despotović, N Radić, PG Plieger
Quinolino[7,8-h]quinoline is a superbasic compound, with a pKaH in acetonitrile greater than that of 1,8-bis(dimethylaminonaphthalene) (DMAN), although its synthesis and the synthesis of its derivatives can be problematic. The use of halogen derivatives 4,9-dichloroquinolino[7,8-h]quinoline (16) and 4,9-dibromoquinolino[7,8-h]quinoline (17) as precursors has granted the formation of a range of substituted quinolinoquinolines. The basicity and other properties of quinolinoquinolines can be modified by the inclusion of suitable functionalities. The experimentally obtained pKaH values of quinolino[7,8-h]quinoline derivatives show that N4,N4,N9,N9-tetraethylquinolino[7,8-h]quinoline-4,9-diamine (26) is more superbasic than quinolino[7,8-h]quinoline. Computationally derived pKaH values of quinolinoquinolines functionalized with dimethylamino (NMe2), 1,1,3,3-tetramethylguanidino (N-C(NMe2)2) or N,N,N′,N′,N″,N″-hexamethylphosphorimidic triamido (N-P(NMe2)3) groups are significantly greater than those of quinolino[7,8-h]quinoline. Overall, electron-donating functionalities are observed to increase the basicity of the quinolinoquinoline moiety, while the substitution of electron-withdrawing groups lowers the basicity.

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Preferred citation

Rowlands, G. J., Severinsen, R. J., Buchanan, J. K., Shaffer, K. J., Jameson, H. T., Thennakoon, N., Leito, I., Lõkov, M., Kütt, A., Vianello, R., Despotović, I., Radić, N. & Plieger, P. G. (2020). Synthesis and Basicity Studies of Quinolino[7,8- h]quinoline Derivatives. Journal of Organic Chemistry, 85(17), 11297-11308. https://doi.org/10.1021/acs.joc.0c01428

Journal title

Journal of Organic Chemistry

Volume

85

Issue

17

Publication date

04/09/2020

Pagination

11297-11308

Publisher

American Chemical Society (ACS)

Publication status

Published

Online publication date

30/07/2020

ISSN

0022-3263

eISSN

1520-6904

Language

en