Synthesis of Isoindolo[2,1-a]quinazoline, Isoindolo[2,1-a]pyrrolo [2,1-c]quinoxalinone, and Indolo[1,2-a]isoindolo[1,2-c]quinoxalinone Derivatives in a Deep Eutectic Solvent

Rajkumari Vijilata Devi; Ashok M. Garande; Prakash M. Bhate

doi:10.1055/s-0036-1588074

Synlett, Table of Contents

Synlett 2016; 27(20): 2807-2810
DOI: 10.1055/s-0036-1588074

letter

Synthesis of Isoindolo[2,1-a]quinazoline, Isoindolo[2,1-a]pyrrolo [2,1-c]quinoxalinone, and Indolo[1,2-a]isoindolo[1,2-c]quinoxalinone Derivatives in a Deep Eutectic Solvent

Authors

Rajkumari Vijilata Devi

Department of Dyestuff Technology, Institute of Chemical Technology, N. P. Marg, Matunga, Mumbai 400 019, Maharashtra, India Email: pm.bhate@ictmumbai.edu.in
Ashok M. Garande

Department of Dyestuff Technology, Institute of Chemical Technology, N. P. Marg, Matunga, Mumbai 400 019, Maharashtra, India Email: pm.bhate@ictmumbai.edu.in
Prakash M. Bhate*

Department of Dyestuff Technology, Institute of Chemical Technology, N. P. Marg, Matunga, Mumbai 400 019, Maharashtra, India Email: pm.bhate@ictmumbai.edu.in

Abstract

All articles of this category

^◊These authors contributed equally.

Abstract

2-Formylbenzoic acid reacts with various derivatives of 2-aminobenzamide, 2-(1H-pyrrol-1-yl)aniline or 2-(1H-indol-1-yl)aniline in a deep eutectic solvent to give the corresponding derivatives of 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione, isoindolo[2,1-a]pyrrolo[2,1-c]quinoxalin-10(14bH)-one, and indolo[1,2-a]isoindolo[1,2-c]quinoxalin-11(15bH)-one, respectively . This protocol is operationally simple, mild, and efficient.

Key words

eutectics - formylbenzoic acid - isoindoloquinazolinediones - isoindolopyrroloquinoxalinones - indoloisoindoloquinoxalinones derivatives - aminobenzamides

Full Text

References

References and Notes
1 Hamprecht D, Micheli F, Tedesco G, Checchia A, Donati D, Petrone M, Terreni S, Wood M. Bioorg. Med. Chem. Lett. 2007; 17: 428
2 Li Y, Wu C, Liu D, Proksch P, Guo P, Lin W. J. Nat. Prod. 2014; 77: 138
3 Lu W.-W, Gao Y.-J, Su M.-Z, Luo Z, Zhang W, Shi G.-B, Zhao Q.-C. Helv. Chim. Acta 2013; 96: 109
4 Oukoloff K, Buron F, Routier S, Jean L, Renard P.-Y. Eur. J. Org. Chem. 2015; 2450
5 Speck K, Magauer T. Beilstein J. Org. Chem. 2013; 9: 2048
6 Wang G, Wu W, Zhu Q, Fu S, Wang X, Hong S, Guo R, Bao B. Chin. J. Chem. 2015; 33: 1089
7 Wrobel J, Dietrich A, Woolson SA, Millen J, McCaleb M, Harrison MC, Hohman TC, Sredy J, Sullivan D. J. Med. Chem. 1992; 35: 4613
8 Zhang G, Sun S, Zhu T, Lin Z, Gu J, Li D, Gu Q. Phytochemistry 2011; 72: 1436
9 Kumar KS, Kumar PM, Kumar KA, Sreenivasulu M, Jafar AA, Rambabu D, Krishna GR, Reddy CM, Kapavarapu R, Shivakumar K, Priya KK, Parsa KV. L, Pal M. Chem. Commun. 2011; 47: 5010
10 Sashidhara KV, Palnati GR, Dodda RP, Avula SR, Swami P. Synlett 2013; 24: 105
11 Gromachevskaya EV, Fin’ko AV, Butin AV, Pushkareva KS, Strelkov VD, Isakova LI, Krapivin GD. Chem. Heterocycl. Compd. (Engl. Transl.) 2013; 49: 1331
12 Reddy GR, Reddy TR, Chary RG, Joseph SC, Mukherjee S, Pal M. Tetrahedron Lett. 2013; 54: 6744
13 Avalani JR, Patel DS, Raval DK. J. Mol. Catal. B: Enzym. 2013; 90: 70
14 Santra S, Bagdi AK, Majee A, Hajra A. RSC Adv. 2013; 3: 24931
15 Lu L, Yang K, Zhang M.-M, Wang X.-S. J. Heterocycl. Chem. 2014; 51: 630
16 Jin R.-Z, Zhang W.-T, Zhou Y.-J, Wang X.-S. Tetrahedron Lett. 2016; 57: 2515
17 Mahdavi M, Najafi R, Saeedi M, Alipour E, Shafiee A, Foroumadi A. Helv. Chim. Acta 2013; 96: 419
18 Bunce RA, Nammalwar B. J. Heterocycl. Chem. 2011; 48: 991
19 Cheeseman GW. H, Rafiq M. J. Chem. Soc. C 1971; 2732
20 Raines S, Chai SY, Palopoli FP. J. Heterocycl. Chem. 1976; 13: 711
21 Kim HS, Kurasawa Y, Yoshii C, Masuyama M, Takada A, Okamoto Y. J. Heterocycl. Chem. 1990; 27: 1115
22 Zhang X.-c, Huang W.-y. Tetrahedron Lett. 1997; 38: 4827
23 He Z, Bae M, Wu J, Jamison TF. Angew. Chem. Int. Ed. 2014; 53: 14451
24 Verma AK, Jha RR, Sankar VK, Aggarwal T, Singh RP, Chandra R. Eur. J. Org. Chem. 2011; 6998
25 Othman M, Pigeon P, Netchitailo P, Daich A, Decroix B. Heterocycles 2000; 52: 273
26 Veeraraghavan S, Popp FD. J. Heterocycl. Chem. 1981; 18: 775
27 Atfah A, Abu-Shuheil MY, Hill J. Tetrahedron 1990; 46: 6483
28 Yi CS, Yun SY. J. Am. Chem. Soc. 2005; 127: 17000
29 Kundu B, Sawant D, Chhabra R. J. Comb. Chem. 2005; 7: 317
30 Rokade SM, Bhate PM. Carbohydr. Res. 2015; 416: 21
31 Rokade SM, Bhate PM. Carbohydr. Res. 2015; 415: 28
32 Singh BS, Lobo HR, Pinjari DV, Jarag KJ, Pandit AB, Shankarling GS. Ultrason. Sonochem. 2013; 20: 287
33 Smith EL, Abbott AP, Ryder KS. Chem. Rev. 2014; 114: 11060
34 Tang B, Row KH. Monatsh. Chem. 2013; 144: 1427
35 Vidal C, García-Álvarez J, Hernán-Gómez A, Kennedy AR, Hevia E. Angew. Chem. Int. Ed. 2014; 53: 5969
36 Zhang Q, De Oliveira Vigier K, Royer S, Jérôme F. Chem. Soc. Rev. 2012; 41: 7108
37 6,6a-Dihydroisoindolo[2,1-a]quinazoline-5,11-diones 3a–g, Isoindolo[2,1-a]pyrrolo[2,1-c]quinoxalin-10(14bH)-ones 5a–f, and Indolo[1,2-a]isoindolo[1,2-c]quinoxalin-11(15bH)-ones 7a,b; General Procedure To a mixture of 2-formylbenzoic acid (1; 1 mmol) and the appropriate amine 2, 4, or 6 (1 mmol) was added the DES (1.5 g), prepared from ChCl and TsOH.³¹ The resulting mixture was stirred at r.t. until the starting materials were completely consumed (TLC). The reaction mass was then diluted with H₂O (5 mL), and the desired product, obtained as a precipitate, was isolated by filtration and crystallized from the appropriate solvent. The filtrate was evaporated under vacuum at 70 °C for 2 h, and the residual DES was reused in further reaction cycles. 6,6a-Dihydroisoindolo[2,1-a]quinazoline-5,11-dione (3a) White solid; yield: 237 mg (95%); ¹H NMR (500 MHz, DMSO-d ₆): δ = 9.406 (s, 1 H), 8.089 (d, J = 7.5 Hz, 1 H), 7.983 (d, J = 7 Hz, 1 H), 7.898 (d, J = 7 Hz, 2 H), 7.801 (t, J = 7 Hz, 1 H), 7.724–7.688 (m, 2 H), 7.361 (t, J = 7 Hz, 1 H), 6.526 (s, 1 H)