Tandem Synthesis of 10-Dimethylaminobenzo[h]quinazolines from 2-Ketimino-1,8-bis(dimethylamino)naphthalenes via Nucleophilic Replacement of the Unactivated Aromatic NMe2 Group.

作者: Vladimir Y. Mikshiev , Alexander S. Antonov , Alexander F. Pozharskii

DOI: 10.1021/ACS.ORGLETT.6B01178

关键词:

摘要: … It is even more convenient to use preliminarily prepared 2-ketimino-1,8-bis(dimethylamino)naphthalenes as starting material. The substitution of both peri-NMe 2 groups furnishing …

参考文章(18)
Alexander S. Antonov, Alexander F. Pozharskii, Valery A. Ozeryanskii, Aleksander Filarowski, Kyrill Yu. Suponitsky, Peter M. Tolstoy, Mikhail A. Vovk, Ring lithiation of 1,8-bis(dimethylamino)naphthalene: another side of the ‘proton sponge coin’ Dalton Transactions. ,vol. 44, pp. 17756- 17766 ,(2015) , 10.1039/C5DT02482J
Shizen Sekiguchi, Masaru Hosokawa, Tohru Suzuki, Mitsuo Sato, Kinetic studies of the reaction of 1-dialkylamino-2,4-dinitronaphthalenes with butylamine in dimethyl sulfoxide Journal of The Chemical Society-perkin Transactions 1. pp. 1111- 1118 ,(1993) , 10.1039/P29930001111
Imtiaz Khan, Aliya Ibrar, Waqas Ahmed, Aamer Saeed, Synthetic approaches, functionalization and therapeutic potential of quinazoline and quinazolinone skeletons: The advances continue European Journal of Medicinal Chemistry. ,vol. 90, pp. 124- 169 ,(2015) , 10.1016/J.EJMECH.2014.10.084
Valery A. Ozeryanskii, Alexander F. Pozharskii, Alexander S. Antonov, Alexander Filarowski, Out-Basicity of 1,8-bis(dimethylamino)naphthalene: the experimental and theoretical challenge Organic and Biomolecular Chemistry. ,vol. 12, pp. 2360- 2369 ,(2014) , 10.1039/C3OB41986J
Kh. M. Shakhidoyatov, B. Zh. Elmuradov, Tricyclic Quinazoline Alkaloids: Isolation, Synthesis, Chemical Modification, and Biological Activity Chemistry of Natural Compounds. ,vol. 50, pp. 781- 800 ,(2014) , 10.1007/S10600-014-1086-6
Shizen Sekiguchi, Tohru Suzuki, Yukitoshi Hirosawa, Hiromi Ishikura, Aromatic nucleophilic substitution. 27. Aromatic nucleophilic substitution reactions of 1-(alkylamino)-2,4-dinitronaphthalenes with various primary amines in dimethyl sulfoxide Journal of Organic Chemistry. ,vol. 55, pp. 1829- 1834 ,(1990) , 10.1021/JO00293A029
Alexander F. Pozharskii, Oksana V. Ryabtsova, Valery A. Ozeryanskii, Alexander V. Degtyarev, Olga N. Kazheva, Gregory G. Alexandrov, Oleg A. Dyachenko, Organometallic synthesis, molecular structure, and coloration of 2,7-disubstituted 1,8-bis(dimethylamino)naphthalenes. How significant is the influence of "buttressing effect" on their basicity? Journal of Organic Chemistry. ,vol. 68, pp. 10109- 10122 ,(2003) , 10.1021/JO035350T
Shizen Sekiguchi, Thoru Suzuki, Masaru Hosokawa, Aromatic nucleophilic substitution reactions of 1-dialkylamino-2,4-dinitronaphthalenes with various amines in dimethyl sulphoxide. Part 26. Journal of The Chemical Society-perkin Transactions 1. pp. 1783- 1788 ,(1989) , 10.1039/P29890001783
Xiang Su, Chao Chen, Yong Wang, Junjie Chen, Zhenbang Lou, Ming Li, One-pot synthesis of quinazoline derivatives via [2+2+2] cascade annulation of diaryliodonium salts and two nitriles Chemical Communications. ,vol. 49, pp. 6752- 6754 ,(2013) , 10.1039/C3CC43216E