Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2019; 51(16): 3101-3108
DOI: 10.1055/s-0037-1611808
DOI: 10.1055/s-0037-1611808
paper
Silver Triflate Catalyzed Synthesis of Isoquinolino[2,1-a]quinazolino[3,2-c]quinazoline Derivatives via Alkyne Hydroamination
This work was financially supported by NSFC of China (No. 21702078), the NSF of Jiangsu Province (No. BK20170231), and TAPP.Further Information
Publication History
Received: 26 November 2018
Accepted after revision: 01 April 2019
Publication Date:
24 April 2019 (online)
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611808.
- Supporting Information
- CIF File
-
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