Synthesis, Table of Contents Synthesis 2019; 51(16): 3101-3108DOI: 10.1055/s-0037-1611808 paper © Georg Thieme Verlag Stuttgart · New YorkSilver Triflate Catalyzed Synthesis of Isoquinolino[2,1-a]quinazolino[3,2-c]quinazoline Derivatives via Alkyne Hydroamination Authors Wan-Chen Pan Mei-Mei Zhang Jian-Quan Liu* Xiang-Shan Wang * Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract Using 2-(2-aminophenyl)quinazolin-4(3H)-one and 2-(2-phenylethynyl)benzaldehyde as the reactants, silver triflate (AgOTf) was proved to be an efficient catalyst to promote not only quinazoline cyclization, but also the intramolecular hydroamination of alkyne for the synthesis of 6-aryl-17H,18aH-isoquinolino[2,1-a]quinazolino[3,2-c]quinazolin-17-one derivatives in high yields. Key words Key wordsisoquinoline - quinazoline - hydroamination - AgOTf - synthesis Full Text References References 1a See CS, Kitagawa M, Liao P.-J, Lee KH, Wong J, Lee SH, Dymock BW. Eur. J. Med. Chem. 2018; 156: 344 1b Rotthier G, Cappoen D, Nguyen QT, Tuyet AD, Mathys V, Nguyen VT, Huygen K, Mae L, Cos P, Abbaspour TK. Org. Biomol. Chem. 2016; 14: 2041 1c Cui M.-T, Jiang L, Goto M, Hsu P.-L, Li L, Zhang Q, Wei L, Yuan S.-J, Hamel E, Morris-Natschke SL, Lee KH, Xie L. J. Med. Chem. 2017; 60: 5586 2a Xie Q, Wu G.-Z, Yang N, Shen Y.-H, Tang J, Zhang W.-D. Biochem. Biophys. Res. Commun. 2018; 502: 202 2b Mirhadi E, Rezaee M, Malaekeh-Nikouei B. Biomed. Pharmacother. 2018; 104: 465 2c Jin T.-Y, Li S.-Q, Jin C.-R, Shan H, Wang R.-M, Zhou M-X, Li A.-L, Li L.-Y, Hu S.-Y, Shen T, Xiang L. J. Nat. Prod. 2018; 81: 768 2d Maleki SN, Aboutaleb N, Souri F. J. Chem. Neuroanat. 2018; 87: 54 3a Zhou J, Ji M, Yao H.-P, Cao R, Zhao H.-L, Wang X.-Y, Chen X.-G, Xu B.-L. Org. Biomol. Chem. 2018; 16: 3189 3b Zhang Y.-L, Chen L, Xu H.-J, Li X.-B, Zhao L.-J, Wang W, Li B.-L, Zhang X.-Q. Eur. J. Med. Chem. 2018; 147: 77 3c Kuang Y, Sechi M, Nurra S, Ljungman M, Neamati N. J. Med. Chem. 2018; 61: 1576 4a Ortalli GL, Tiberio I, Mammana G. Minerva Anestesiol. 1993; 59: 133 4b Siler JN, Mager JG, Wyche MQ. Anesthesiology 1985; 62: 645 5a Viola D, Valerio L, Molinaro E, Agate L, Bottici V, Biagini A, Lorusso L, Cappaqli V, Pieruzzi L, Giani C, Sabini E, Passannati P, Puleo L, Matrone A, Pontillo-Contillo B, Battaqlia V, Mazzeo S, Vitti P, Elisei R. Endocr. Relat. Cancer 2016; 23: 185 5b Martin P, Oliver S, Kennedy SJ, Partridge E, Hutchison M, Clarke D, Giles P. Clin. Ther. 2012; 34: 221 6a Lou M.-H, Deng Z.-H, Mao X.-C, Fu Y, Yang Q, Peng Y.-Y. Org. Biomol. Chem. 2018; 16: 1851 6b Neel AJ, Hehn JP, Tripet PF, Toste F. J. Am. Chem. Soc. 2013; 135: 14044 6c Kumar KS, Kumar PM, Reddy MA, Ferozuddin MD, Sreenivasulu M, Jafar AA, Krishna GR, Reddy CM, Rambabu D, Shiva-Kumar K, Pal S, Pal M. Chem. Commun. 2011; 47: 10263 7a Qiu G.-Y.-S, He Y.-H, Wu J. Chem. Commun. 2012; 48: 3836 7b Solomos MA, Bertke JA, Swift JA. New J. Chem. 2018; 42: 7125 7c Tajfirooz F, Davoodnia A, Pordel M, Ebrahimi M, Beyramabadi SA. Russ. J. Gen. Chem. 2017; 87: 2429 7d Duan F.-J, Liu M.-C, Chen J.-X, Ding J.-C, Hu Y.-F, Wu H.-Y. RSC Adv. 2013; 3: 24001 7e Venkateswarlu S, Satyanarayana M, Ravikiran P, Siddaiah V. J. Heterocycl. Chem. 2013; 50: 1089 7f Shafii B, Saeedi M, Mahdavi M, Foroumadi A, Shafiee A. Synth. Commun. 2014; 44: 215 8 Bahadorikhalili S, Mahdavi M, Ma’mani L, Shafiee A, Mahdavi H, Akbarzadeh T. New J. Chem. 2018; 42: 5499 9a Roy AD, Subramanian A, Roy RR. J. Org. Chem. 2006; 71: 382 9b Marinho E, Proenca MF. RSC Adv. 2016; 6: 6138 9c Venkateswarlu S, Satyanarayana M, Lakshmikanthan V, Siddaiah V. J. Heterocycl. Chem. 2015; 52: 1631 10a Patel M, Saunthwal RK, Verma AK. Acc. Chem. Res. 2017; 50: 240 10b Pohlki F, Doye S. Chem. Soc. Rev. 2003; 32: 104 10c Bytschkov I, Doye S. Eur. J. Org. Chem. 2003; 935 11a Zhang J.-T, Liao Z.-H, Chen L.-F, Jiang H.-F, Zhu S.-F. Chem. Eur. J. 2018; 24: 6927 11b Ren A, Lang B, Lin J.-L, Lu P, Wang Y.-G. J. Org. Chem. 2017; 82: 10953 11c Dawande SG, Harode M, Kalepu J, Katukojvala S. Chem. Commun. 2016; 52: 13699 11d Sharma P, Kumar NP, Krishna NH, Prasanna D, Sridhar B, Shankaraiah N. Org. Chem. Front. 2016; 3: 1503 11e Wang H, Kuang Y, Wu J. Asian J. Org. Chem. 2012; 1: 302 11f Ding Q, Wu J. Org. Lett. 2007; 9: 4959 11g Sun W, Ding Q, Sun X, Fan R, Wu J. J. Comb. Chem. 2007; 9: 690 11h Yu X, Wu J. J. Comb. Chem. 2010; 12: 238 12a Feng B.-B, Liu J.-Q, Wang X.-S. J. Org. Chem. 2017; 82: 1817 12b Liu J.-Q, Ma Y.-G, Zhang M.-M, Wang X.-S. J. Org. Chem. 2017; 82: 4918 12c Ma Y.-G, Liu J.-Q, Wang X.-S. Tetrahedron 2017; 73: 4698 12d Chen D.-S, Zhang M.-M, Li Y.-L, Liu Y, Wang X.-S. Tetrahedron 2014; 70: 2889 12e Pan W.-C, Liu J.-Q, Wang W.-S. Tetrahedron 2018; 74: 1468 12f Pan W.-C, Liu J.-Q, Wang W.-S. Org. Biomol. Chem. 2018; 16: 6070 Supplementary Material Supplementary Material Supporting Information (PDF) CIF File (ZIP)
