RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2015; 26(18): 2575-2577
DOI: 10.1055/s-0035-1560483
DOI: 10.1055/s-0035-1560483
letter
Efficient Access to 2,3-Dihydroquinazolin-4(1H)-ones by Environmentally Benign l-Proline Nitrate as Recyclable Catalyst
Weitere Informationen
Publikationsverlauf
Received: 10. Juli 2015
Accepted after revision: 24. August 2015
Publikationsdatum:
15. September 2015 (online)
![](https://www.thieme-connect.de/media/synlett/201518/lookinside/thumbnails/st-2015-d0532-l_10-1055_s-0035-1560483-1.jpg)
Abstract
An l-proline nitrate assisted protocol is described for the construction of 2,3-dihydroquinazolin-4(1H)-ones. The catalyst can be recovered easily and is reusable for at least six cycles without significant loss of catalytic efficiency.
Key words
2,3-dihydroquinazolin-4(1H)-one - l-proline nitrate - ionic liquid - cyclocondensation reactionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560483.
- Supporting Information
-
References and Notes
- 1 Zhou YJ, Chen DS, Li YL, Liu Y, Wang XS. ACS Comb. Sci. 2013; 15: 498
- 2 McGonagle FI, Sneddon HF, Jamieson C, Watson AJ. ACS Sustainable Chem. Eng. 2014; 2: 523
- 3 Agrawal NR, Bahekar SP, Sarode PB, Zade SS, Chandak HS. RSC Adv. 2015; 5: 47053
- 4 Tao G.-H, He L, Liu W.-S, Xu L, Xiong W, Wang T, Kou Y. Green Chem. 2006; 8: 639
- 5 Hamel E, Lin CM, Plowman J, Wang H, Lee K, Paull KD. Biochem. Pharmacol. 1996; 51: 53
- 6 Alagarsamy V, Solomon VR, Murugan M. Bioorg. Med. Chem. 2007; 15: 4009
- 7 Levin JI, Chan PI, Bailey T, Katocs AS, Venkatesan AM. Bioorg. Med. Chem. Lett. 1994; 4: 1141
- 8 Mustazza C, Borioni A, Sestili I, Sbraccia M, Rodomonte A, Ferretti R, Giudice MR. D. Chem. Pharm. Bull. 2006; 54: 611
- 9 Hirose N, Kuriyama S, Sohda S, Sakaguchi K, Yamamoto H. Chem. Pharm. Bull. 1973; 21: 1005
- 10 Birch HL, Buckley GM, Davies N, Dyke HJ, Frost EJ, Gilbert PJ, Hannah DR, Haughan AF, Madigan MJ, Morgan T, Pitt WR, Ratcliffe AJ, Ray NC, Richard MD, Sharpe A, Taylor AJ, Whitworth JM, Williams SC. Bioorg. Med. Chem. Lett. 2005; 15: 5335
- 11 Bolger JW. US 3257397, 1966
- 12 Bonola G, Da RP, Magistretti MJ, Massarani E, Setnikar I. J. Med. Chem. 1968; 11: 1136
- 13 (Instituto De Angeli SPA) FR 1893, 1963.
- 14 Schipper ES. US 3265697, 1966
- 15 Okumura K, Oine T, Yamada Y, Hayashi G, Nakama M. J. Med Chem. 1968; 11: 348
- 16 Ouyang G, Zhang P, Xu G, Song BS, Jin L, Xue W, Hu D, Lu P, Chen Z. Molecules 2006; 11: 383
- 17 Wang S, Lou H, Liu Y, Yu G, Lu P, Zhu D. J. Mater. Chem. 2001; 11: 2971
- 18a Cheng X, Vellalath S, Goddard R, List B. J. Am. Chem. Soc. 2008; 130: 15786
- 18b Chinigo GM, Paige M, Grindrod S, Hamel E, Dakshanamurthy S, Chruszcz M, Minor W, Brown ML. J. Med. Chem. 2008; 51: 4620
- 18c Hour MJ, Huang LJ, Kuo SC, Xia Y, Bastow K, Nakanishi Y, Hamel E, Lee KH. J. Med. Chem. 2000; 43: 4479
- 18d Chen JX, Wu DZ, He F, Liu MC, Wu HY, Ding JC, Su WK. Tetrahedron Lett. 2008; 49: 3814
- 18e Salehi P, Dabiri M, Zolfigol MA, Baghbanzadeh M. Synlett 2005; 1155
- 18f Rahman M, Ling I, Abdullah N, Hashim R, Hajra A. RSC Adv. 2015; 5: 7755
- 18g Rostami A, Tahmasbi B, Gholami H, Taymorian H. Chin. Chem. Lett. 2013; 24: 211
- 18h Safari J, Gandomi-Ravandi S. J. Mol. Catal. A: Chem. 2013; 371: 135
- 18i Sharma M, Pandey S, Chauhan K, Sharma D, Kumar B, Chauhan PM. J. Org. Chem. 2012; 77: 929
- 18j Ramesh K, Karnakar K, Satish G, Anil Kumar BS. P, Nageswar YV. D. Tetrahedron Lett. 2012; 53: 6936
- 19a Chen J, Su W, Wu H, Liub M, Jin C. Green Chem. 2007; 9: 972
- 19b Davoodnia A, Allameh S, Fakhari AR, Tavakoli-Hoseini N. Chin. Chem. Lett. 2010; 21: 550
- 20 General Procedure A mixture of anthranilamide (1.46 mmol), aldehyde (1.46 mmol), and l-proline nitrate (10 mol%) was stirred at r.t. in MeCN (0.5 mL). The progress of the reaction was monitored by TLC. After completion of reaction, the solid obtained was filtered and recrystallized from EtOH to give 3a–o. To recover the catalyst, the filtrate was evaporated under reduced pressure. The residue obtained was washed with a small quantity of H2O. This was again removed under reduced pressure, and the last traces of H2O were removed azeotropically with a small volume of toluene to obtain the catalyst in a suitable form for the next reaction.
- 21 Representative Characterization Data Compound 3g: white solid; yield 87%; mp 168–170 °C. 1H NMR (400 MHz, DMSO-d 6): δ = 8.24 (s, 1 H, NH), 7.07 (s, 1 H, NH), 7.62 (d, J = 7.6 Hz, 1 H, Ar), 7.34 (d, J = 7.6 Hz, 1 H, Ar), 7.13 (d, J = 6.2 Hz, 1 H, Ar), 6.86–6.65 (m, 5 H, 1 NH, 4 Ar), 6.00 (s, 1 H), 2.88 (sept, J = 7.2 Hz, 1 H, CH(CH3)2), 1.17 [d, J = 7.2Hz, 6 H, CH(CH3)2].
- 22 Compound 3k: white solid; yield 87%; mp 210–211 °C. 1H NMR (400 MHz, DMSO-d 6): δ = 9.86 (s, 1 H, OH), 7.94 (s, 1 H, NH), 6.95 (s, 1 H, NH), 7.62 (d, J = 7.6 Hz, 1 H, Ar), 7.34 (d, J = 7.6 Hz, 1 H, Ar), 7.13 (d, J = 6.2 Hz, 1 H, Ar), 6.86–6.65 (m, 5 H, 1 NH, 4 Ar), 6.00 (s, 1 H).
- 23 Compound 3l: white solid; yield 90%; mp 208–210 °C. 1H NMR (400 MHz, DMSO-d 6): δ = 9.12 (s, 1 H, OH), 7.69 (s, 1 H, NH), 6.29 (s, 1 H, NH), 7.68 (d, J = 7.64 Hz, 1 H, Ar), 7.23–6.64 (m, 8 H, Ar), 5.66 (s, 1 H).
- 24 Compound 3m: white solid; yield 90%; mp 280–281 °C. 1H NMR (400 MHz, DMSO-d 6): δ = 9.55 (s, 1 H, OH), 8.12 (s, 1 H, NH), 6.95 (s, 1 H, NH), 7.60 (d, J = 6.8 Hz, 1 H, Ar), 7.31–7.21 (m, 3 H, Ar), 6.77–6.64 (m, 4 H, Ar), 5.64 (s, 1 H).
- 25 Murthy PV. N. S, Rambabu D, Rama Krishna G, Malla RC, Prasad KR. S, Basaveswara Rao MV, Pal M. Tetrahedron Lett. 2012; 53: 863
- 26 Dindulkar SD, Oh J, Arole VM, Jeong YT. C. R. Chimie 2014; 17: 971
- 27 Qiao RZ, Xu BL, Wang YH. Chin. Chem. Lett. 2007; 18: 656
- 28 Smith TA. K, Stephen H. Tetrahedron 1957; 1: 38
- 29 Shaabani A, Ali MA, Mofakham H. Synth. Commun. 2008; 38: 3751
For chiral phosphoric acid, see:
For TFA, see:
For p-TsOH, see:
For gallium triflate, see:
For silica-H2SO4, see:
For calix[4]arene (p-SAC), see:
For MNP-PSA (N-propylsulfamic acid supported onto magnetic Fe3O4 nanoparticles), see:
For Cu-CNTs, see:
For low-valent titanium reagents, see:
For β-cyclodextrin, see:
For [bmim]PF6, see:
For TBAB, see: