Synthesis of Substituted Quinazolin-4(3H)-imines From Aryldiazonium Salts, Nitriles and 2-Cyanoanilines via A Metal-Free Tandem Approach
作者： Mani Ramanathan , Yi-Hung Liu , Shie-Ming Peng , Shiuh-Tzung Liu
DOI: 10.1021/ACS.ORGLETT.7B02822
关键词:
摘要: A transition metal-free synthesis of multisubstituted quinazolin-4(3H)-imines has been realized by the direct reaction aryldiazonium salts, nitriles, and 2-cyanoanilines in a one-pot fashion. This strategy utilizes situ formation reactive N-arylnitrilium intermediate, which undergoes further tandem cyclization with consecutive N–C bonds. Broad functional group compatibility, mild conditions, shorter time, operational simplicity are notable features this report.
acs.org
ntu.edu.tw
sci-hub.se 参考文章(33)
François-Xavier Felpin, Luma Nassar-Hardy, François Le Callonnec, Eric Fouquet, Recent advances in the Heck–Matsuda reaction in heterocyclic chemistry Tetrahedron. ,vol. 67, pp. 2815- 2831 ,(2011) , 10.1016/J.TET.2011.02.051
Rebeca Saez, M. Dolores Otero, Belen Batanero, Fructuoso Barba, Microwave Reaction of Diazonium Salts with Nitriles Journal of Chemical Research-s. ,vol. 2008, pp. 492- 494 ,(2008) , 10.3184/030823408X340780
Elisabeth M. Perchellet, Sundeep Rayat, Jean-Pierre H. Perchellet, Kusum L. Chandra, John Desper, Vijaya K. Naganaboina, Andrew M. Waters, Bioactivity of Synthetic 2-Halo-3-aryl-4(3H)-quinazoliniminium Halides in L1210 Leukemia and SK-BR-3 Mammary Tumor Cells In Vitro Anticancer Research. ,vol. 31, pp. 2083- 2093 ,(2011)
Yao Chen, Lei Fang, Sixun Peng, Hong Liao, Jochen Lehmann, Yihua Zhang, Discovery of a novel acetylcholinesterase inhibitor by structure-based virtual screening techniques. Bioorganic & Medicinal Chemistry Letters. ,vol. 22, pp. 3181- 3187 ,(2012) , 10.1016/J.BMCL.2012.03.046
Vijaya Kumar Naganaboina, Kusum Lata Chandra, John Desper, Sundeep Rayat, An easy entry into 2-halo-3-aryl-4(3H)-quinazoliniminium halides from heteroenyne-allenes. Organic Letters. ,vol. 13, pp. 3718- 3721 ,(2011) , 10.1021/OL201372N
B. Suresh Kuarm, Y. Thirupathi Reddy, J. Venu Madhav, Peter A. Crooks, B. Rajitha, 3-[Benzimidazo- and 3-[benzothiadiazoleimidazo-(1,2-c)quinazolin-5-yl]-2H-chromene-2-ones as potent antimicrobial agents. Bioorganic & Medicinal Chemistry Letters. ,vol. 21, pp. 524- 527 ,(2011) , 10.1016/J.BMCL.2010.10.082
Lin He, Haoquan Li, Jianbin Chen, Xiao-Feng Wu, Recent advances in 4(3H)-quinazolinone syntheses RSC Advances. ,vol. 4, pp. 12065- 12077 ,(2014) , 10.1039/C4RA00351A
Jason G. Taylor, Angélica Venturini Moro, Carlos Roque D. Correia, Evolution And Synthetic Applications Of The Heck-matsuda Reaction: The Return Of Arenediazonium Salts To Prominence European Journal of Organic Chemistry. ,vol. 2011, pp. 1403- 1428 ,(2011) , 10.1002/EJOC.201001620
Xinyu Chen, Irina G. Tikhonova, Michael Decker, Probing the mid-gorge of cholinesterases with spacer-modified bivalent quinazolinimines leads to highly potent and selective butyrylcholinesterase inhibitors. Bioorganic & Medicinal Chemistry. ,vol. 19, pp. 1222- 1235 ,(2011) , 10.1016/J.BMC.2010.12.034
Emanuela Erba, Donato Pocar, Pasqualina Trimarco, Single step synthesis of 2,3-dialkyl-6-nitro-quinazolin-4(3H)-imines and 3,5-dialkyl-9-nitro-imidazo[1,2-c]quinazolin-2(3H)-ones Tetrahedron. ,vol. 61, pp. 5778- 5781 ,(2005) , 10.1016/J.TET.2005.04.028