Synthesis of Isoquinoline-Fused Quinazolinones through Ag(I)-Catalyzed Cascade Annulation of 2-Aminobenzamides and 2-Alkynylbenzaldehydes

Amol D. Sonawane; Yunnus B. Shaikh; Dinesh R. Garud; Mamoru Koketsu

doi:10.1055/s-0037-1610910

Synthesis, Table of Contents

Synthesis 2019; 51(02): 500-507
DOI: 10.1055/s-0037-1610910

paper

Synthesis of Isoquinoline-Fused Quinazolinones through Ag(I)-Catalyzed Cascade Annulation of 2-Aminobenzamides and 2-Alkynylbenzaldehydes

Amol D. Sonawane

^aDepartment of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Gifu 501-1193, Japan

,

Yunnus B. Shaikh

^aDepartment of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Gifu 501-1193, Japan

,

Dinesh R. Garud

^bDepartment of Chemistry, Sir Parashurambhau College, Tilak road, Pune 411030, India Email: koketsu@gifu-u.ac.jp

,

Mamoru Koketsu*

^aDepartment of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Gifu 501-1193, Japan

› Author Affiliations

Abstract

All articles of this category

Abstract

A new route for the expedient synthesis of a specific regioisomer of isoquinoline-fused quinazolinones is reported. Silver(I)-catalyzed cascade cyclization of 2-aminobenzamides and 2-alkynylbenzaldehydes followed by in situ oxidation gives 12-butyl- or 12-aryl-6H-isoquinolino[2,1-a]quinazolin-6-ones in 69–91% yields. The structure of the isoquinoline-fused quinazolinone was confirmed by X-ray crystallography analysis.

Key words

isoquinoline - quinazolinone - regioisomer - silver catalyst - cascade annulation

Full Text

References

References
1 Affiliated to Savitribai Phule Pune University, Pune 411007 India (formerly University of Pune).

For reviews, see:

2a Gladysz JA. Chem. Rev. 2011; 111: 1167
2b Transition Metals for Organic Synthesis . Beller M. Bolm C. Wiley-VCH; New York: 2004
2c Metal-Catalyzed Cross-Coupling Reactions . de Meijere A. Diederich F. Wiley-VCH; New York: 2004
2d Organometallics in Process Chemistry . Larsen RD. Springer; Berlin: 2004
2e Chen X. Engle KM. Wang D.-H. Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
2f Gutekunst WR. Baran PS. Chem. Soc. Rev. 2011; 40: 1976
2g Stokes BJ. Driver TG. Eur. J. Org. Chem. 2011; 4071
2h Mei T.-S. Kou L. Ma S. Engle KM. Yu JQ. Synthesis 2012; 44: 1778
2i Yamaguchi J. Yamaguchi AD. Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
2j Wencel-Delord J. Glorius F. Nat. Chem. 2013; 5: 369
2k Yoshikai N. Wei Y. Asian J. Org. Chem. 2013; 2: 466
2l Ardkhean RD. Caputo FJ. Morrow SM. Shi H. Xiong Y. Anderson EA. Chem. Soc. Rev. 2016; 45: 1557
2m Deiters A. Martin SF. Chem. Rev. 2004; 104: 2199
2n Zeni G. Larock RC. Chem. Rev. 2004; 104: 2285
2o Nakamura I. Yamamoto Y. Chem. Rev. 2004; 104: 2127

For perspectives on atom-, step-, and redox-economy, respectively, see

3a Trost BM. Science (Washington, D. C.) 1991; 254: 1471
3b Trost BM. Angew. Chem. Int. Ed. 1995; 34: 259
3c Newhouse T. Baran PS. Hoffmann RW. Chem. Soc. Rev. 2009; 38: 3010
3d Burns NZ. Baran PS. Hoffmann RW. Angew. Chem. Int. Ed. 2009; 48: 2854

4a Weibel J.-M. Blanc A. Pale P. Chem. Rev. 2008; 108: 3149
4b Álvarez-Corral M. Muñoz-Dorado M. Rodríguez García I. Chem. Rev. 2008; 108: 3174
4c Naodovic M. Yamamoto H. Chem. Rev. 2008; 108: 3132
4d Yamamoto Y. Chem. Rev. 2008; 108: 3199
4e Fang G. Bi X. Chem. Soc. Rev. 2015; 44: 8124
4f Silver in Organic Chemistry . Harmata M. Wiley; Hoboken: 2010
4g Rasika Dias HV. Lovely CJ. Chem. Rev. 2008; 108: 3223
4h Munoz MP. Chem. Soc. Rev. 2014; 43: 3164
4i Lo VK.-Y. Chan AO.-Y. Che C.-M. Org. Biomol. Chem. 2015; 13: 6667
4j Sekine K. Yamada T. Chem. Soc. Rev. 2016; 45: 4524

5a Gorin DJ. Toste FD. Nature (London) 2007; 446: 395
5b Fürstner A. Davies PW. Angew. Chem. Int. Ed. 2007; 46: 3410
5c Fürstner A. Chem. Soc. Rev. 2009; 38: 3208
5d Fang G. Cong X. Zanoni G. Liu Q. Bi X. Adv. Synth. Catal. 2017; 359: 1422
5e Liu J. Fang Z. Zhang Q. Liu Q. Bi X. Angew. Chem. Int. Ed. 2013; 52: 6953
5f Liu J. Liu Z. Liao P. Bi X. Org. Lett. 2014; 16: 6204
5g Meng X. Liao P. Liu J. Bi X. Chem. Commun. 2014; 50: 11837
5h Liu J. Liu Z. Wu N. Liao P. Bi X. Chem. Eur. J. 2014; 20: 2154
5i Liu Z. Liu J. Zhang L. Liao P. Song J. Bi X. Angew. Chem. Int. Ed. 2014; 53: 5305
5j Liu Z. Liao P. Bi X. Org. Lett. 2014; 16: 3668
5k Ning Y. Wu N. Yu H. Liao P. Li X. Bi X. Org. Lett. 2015; 17: 2198
5l Huters AD. Quasdorf KW. Styduhar ED. Garg NK. J. Am. Chem. Soc. 2011; 133: 15797
5m Quasdorf KW. Huters AD. Lodewyk MW. Tantillo DJ. Garg NK. J. Am. Chem. Soc. 2012; 134: 1396

6a Majumdar KC. Chattopadhyay SK. Heterocycles in Natural Product Synthesis . Wiley-VCH; Weinheim: 2011
6b Comprehensive Heterocyclic Chemistry III . Katritzky AR. Ramsden CA. Scriven EV. F. Taylor RJ. K. Elsevier; Amsterdam: 2008
6c Lynch MA. Duval O. Sukhanova A. Devy J. MacKay SP. Waigh RD. Nabiev I. Bioorg. Med. Chem. Lett. 2001; 11: 2643
6d Jones G. Abarca B. Adv. Heterocycl. Chem. 2010; 100: 195
6e Chittchang M. Batsomboon P. Ruchirawat S. Ploypradith P. ChemMedChem 2009; 4: 457
6f Padmavathi V. Radha Lakshmi T. Mahesh K. Padmaja A. Chem. Pharm. Bull. 2009; 57: 1200
6g Eamvijarn A. Gomes NM. Dethoup T. Buaruang J. Manoch L. Silva A. Pedro M. Marini I. Roussis V. Kijjoa A. Tetrahedron 2013; 69: 8583

7a Kshirsagar UA. Org. Biomol. Chem. 2015; 13: 9336
7b Ma Z.-Z. Hano Y. Nomura T. Chen Y.-J. Heterocycles 1997; 46: 541
7c Yoshida S. Aoyagi T. Harada S. Matsuda N. Ikeda T. Naganawa H. Hamada M. Takeuchi T. J. Antibiot. 1991; 44: 111
7d Deng Y. Xu R. Ye Y. J. Chin. Pharm. Sci. 2000; 9: 116
7e Wattanapiromsakul C. Forster PI. Waterman PG. Phytochemistry 2003; 64: 609
7f Michael JP. Nat. Prod. Rep. 2004; 21: 650
7g List B. Synlett 2001; 1675
7h Harb HY. Procter DJ. Synlett 2012; 23: 6
7i Müller TJ. J. Synthesis 2012; 44: 159
7j Kocienski P. Synfacts 2012; 8: 5

For selected examples, see:

8a Cao SL. Feng YP. Jiang YY. S. Liu Y. Ding GY. Li RT. Bioorg. Med. Chem. Lett. 2005; 15: 1915
8b Kung PP. Casper MD. Cook KL. Wilson-Lingardo L. Risen LM. Vickers TA. Ranken R. Blyn LB. Wyatt JR. Cook PD. J. Med. Chem. 1999; 42: 4705
8c De Laszlo SE. Quagliato CS. Greenlee WJ. Patchett AA. Chang RS. L. Lotti VJ. Chen TB. Scheck SA. Faust KA. J. Med. Chem. 1993; 36: 3207
8d Cherm JW. Tao PL. Wang KC. Guicait A. Liu SW. Yen MH. Chien SL. Rong JK. J. Med. Chem. 1998; 41: 3128
8e Malamas MS. Millen J. J. Med. Chem. 1991; 34: 1492
8f Wolfe JF. Rathman TL. Sleevi MC. Campbell JA. Greenwood TD. J. Med. Chem. 1990; 33: 161
8g Mhaske SB. Argade NP. Tetrahedron 2006; 62: 9787
8h Horton DA. Bourne GT. Smythe ML. Chem. Rev. 2003; 103: 893
8i Steinmuller SR. Puschett JB. Kidney Int. 1972; 1: 169
8j Abbas SE. Awadallah FM. Ibrahin NA. Said EG. Kamel GM. Eur. J. Med. Chem. 2012; 53: 141
8k Rudolph J. Esler WP. Connor SO. Coish PD. Wickens PL. Brands M. Bierer DE. Bloomquist BT. Bondar G. Chen L. J. Med. Chem. 2007; 50: 5202
8l Leivers AL. Tallant M. Shotwell JB. Dickerson S. Leivers MR. McDonald OB. Gobel J. Creech KL. Strum SL. Mathis A. J. Med. Chem. 2014; 57: 2091
8m Aly MM. Mohamed YA. El-Bayouki KA. Basyouni WM. Abbas SY. Eur. J. Med. Chem. 2010; 45: 3365
8n Sharma M. Chauhan K. Shivahare R. Vishwakarma P. Suthar MK. Sharma A. Gupta S. Saxena JK. Lal J. Chandra P. J. Med. Chem. 2013; 56: 4374
8o Kamal A. Bharathi EV. Ramaiah MJ. Dastagiri D. Reddy JS. Viswanath A. Sultana F. Pushpavalli S. Pal-Bhadra M. Srivastava HK. Bioorg. Med. Chem. 2010; 18: 526

Reviews on quinazolinone alkaloids:

9a Abdou IM. Al-Neyadi SS. Heterocycl. Commun. 2015; 21: 115
9b Khan I. Ibrar A. Abbas N. Saeed A. Eur. J. Med. Chem. 2015; 90: 124
9c He L. Li H. Chen J. Wu X.-F. RSC Adv. 2014; 4: 12065

For selected examples, see:

10a Padala SR. Padi PR. Thipireddy V. Heterocycles 2003; 60: 183
10b Witt A. Bergman J. Curr. Org. Chem. 2003; 7: 659
10c Ma Z. Hano Y. Nomura T. Heterocycles 2005; 65: 2203
10d Connolly DJ. Cusack D. OSullivan TP. Guiry PJ. Tetrahedron 2005; 61: 10153
10e Demeunynck M. Baussanne I. Curr. Med. Chem. 2013; 20: 794
10f Khan I. Ibrar A. Abbas N. Saeed A. Eur. J. Med. Chem. 2014; 76: 193
10g Duan F. Liu M. Chen J. Ding J. Hu Y. Wu H. RSC Adv. 2013; 3: 24001

11a Bentley KW. Nat. Prod. Rep. 2006; 23: 444
11b Bentley KW. Nat. Prod. Rep. 2005; 22: 249
11c Chrzanowska M. Rozwadowska MD. Chem. Rev. 2004; 104: 3341

12 Isoquinoline-fused quinazolinones were described to display anti-inflammatory activity, see: Ozaki K. Yamada Y. Oine T. Chem. Pharm. Bull. 1984; 32: 2160

13a Yang Y. Zhu C. Zhang M. Huang S. Lin J. Pan X. Su W. Chem. Commun. 2016; 52: 12869
13b Tsukano C. Okuno M. Nishiguchi H. Takemoto Y. Adv. Synth. Catal. 2014; 356: 1533
13c Venkateswarlu S. Satyanarayana M. Lakshmikanthan V. Siddaiah V. J. Heterocycl. Chem. 2015; 52: 1631
13d Venkateswarlu S. Satyanarayana M. Ravikiran P. Siddaiah V. J. Heterocycl. Chem. 2013; 50: 1089
13e Yu Y. Yue Y. Wang D. Li X. Chen C. Peng J. Synthesis 2016; 48: 3941
13f Sun X. Hu Y. Nie S.-Z. Yan Y.-Y. Zhang X.-J. Yan M. Adv. Synth. Catal. 2013; 355: 2179
13g Patil NT. Konala A. Sravanti S. Singh A. Ummanni R. Sridhar B. Chem. Commun. 2013; 49: 10109
13h Xu T. Alper H. Org. Lett. 2015; 17: 1569
13i Oh BK. Ko EB. Han JW. Oh CH. Synth. Commun. 2015; 45: 768
13j Ma Y.-G. Zhang Y. Feng B.-B. Wang X.-S. Res. Chem. Intermed. 2016; 42: 1045
13k Georgey H. Molecules 2014; 19: 3777
13l Ngarita K. Jan B. J. Org. Chem. 2016; 81: 7711
13m Lingayya R. Vellakkaran M. Nagaiah K. Nanubolu JB. Asian J. Org. Chem. 2015; 4: 462
13n Adepu RB. Prasad M. Ashfaq A. Ehtesham NZ. Pal M. RSC Adv. 2014; 4: 49324
13o Volovnenko TA. Tarasov AV. Turov AV. Volovenko YM. Ukr. Khim. Zh. 2007; 73: 44
13p Dighe SU. Batra S. Tetrahedron 2013; 69: 9875

14 Kumar KS. Kumar PM. Reddy MA. Ferozuddin M. Sreenivasulu M. Jafar AA. Krishna GR. Reddy CM. Rambabu D. Kumar KS. Pale S. Pal M. Chem. Commun. 2011; 47: 10263

15a Patil NT. Mutyala AK. Konala A. Tella RB. Chem. Commun. 2012; 48: 3094
15b Patil NT. Mutyala AK. Pediredla GV. V. L. Penmatcha VK. R. Sridhar B. Eur. J. Org. Chem. 2010; 1999

16 CCDC 1819564 for 4a contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
17 Yoshida K. Nishii K. Kano Y. Wada S. Yanagisawa A. J. Org. Chem. 2014; 79: 4231

Supplementary Material

Supporting Information