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 2020; 31(03): 275-279
DOI: 10.1055/s-0037-1610740
DOI: 10.1055/s-0037-1610740
letter
Copper-Catalyzed One-Pot Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones from 2-Nitrobenzonitriles and Carbonyl Compounds Mediated by Diboronic Acid in Methanol–Water
Natural Science Foundation of Hubei Province of China (2018CFB241)Weitere Informationen
Publikationsverlauf
Received: 29. September 2019
Accepted after revision: 02. Dezember 2019
Publikationsdatum:
12. Dezember 2019 (online)
![](https://www.thieme-connect.de/media/synlett/202003/lookinside/thumbnails/st-2019-l0518-l_10-1055_s-0037-1610740-1.jpg)
§ The authors contributed equally.
Abstract
A copper-catalyzed one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones with diboronic acid as a reductant in an aqueous medium is described. Various 2,3-dihydroquinazolin-4(1H)-ones were prepared with good functional-group tolerance in good yields under mild conditions from readily available 2-nitrobenzonitriles and various carbonyl compounds.
Key words
copper catalysis - diboronic acid - dihydroquinazolinones - carbonyl compounds - nitrobenzonitrilesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610740.
- Supporting Information
-
References and Notes
- 1a Badolato M, Aiello F, Neamati N. RSC Adv. 2018; 8: 20894
- 1b Roopan SM, Khan FN, Jin JS, Kumar RS. Res. Chem. Intermed. 2011; 37: 919
- 1c Williams R, Niswender CM, Luo Q, Le U, Conn PJ, Lindsley CW. Bioorg. Med. Chem. Lett. 2009; 19: 962
- 1d Horton DA, Bourne GT, Smythe ML. Chem. Rev. 2003; 103: 893
- 2a Liu P, Deng DS, Wang L. J. Clust. Sci. 2018; 29: 1031
- 2b Sarfraz M, Sultana N, Rashid U, Akram MS, Sadiq A, Tariq MI. Bioorg. Chem. 2017; 70: 237
- 2c Huang G, Liu B, Teng MY, Chen Y. Lett. Org. Chem. 2016; 13: 453
- 2d Rahman M, Ling I, Abdullah N, Hashim R, Hajra A. RSC Adv. 2015; 5: 7755
- 2e Labade VB, Shinde PV, Shingare MS. Tetrahedron Lett. 2013; 54: 5778
- 2f Rostami A, Tavakoli A. Chin. Chem. Lett. 2011; 22: 1317
- 3a Luo Y, Wu Y, Wang Y, Sun H, Xie Z, Zhang W, Gao Z. RSC Adv. 2016; 6: 66074
- 3b Shang Y.-H, Fan L.-Y, Li X.-X, Liu M.-X. Chin. Chem. Lett. 2015; 26: 1355
- 3c Wang M, Gao J, Song Z, Wang L. J. Heterocycl. Chem. 2012; 49: 1250
- 3d Chen JX, Wu HY, Su WK. Chin. Chem. Lett. 2007; 18: 536
- 3e Wang S, Yang K, Wang X. Chin. J. Org. Chem. 2011; 8: 1235
- 3f Abdollahi-Alibeik M, Shabani E. Chin. Chem. Lett. 2011; 22: 1163
- 3g Wang X.-W, Guo H, Liu M.-J, Wang X.-Y, Deng D.-S. Chin. Chem. Lett. 2014; 25: 243
- 4a Kausar N, Roy I, Chattopadhyay D, Das AR. RSC Adv. 2016; 6: 22320
- 4b Sharma M, Pandey S, Chauhan K, Sharma D, Kumar B, Chauhan PM. S. J. Org. Chem. 2012; 77: 929
- 4c Wang X.-S, Yang K, Zhou J, Tu S.-J. J. Comb. Chem. 2010; 12: 417
- 4d Wang M, Gao JJ, Song ZG, Wang L. Chem. Heterocycl. Compd. 2011; 47: 851
- 5a Bunce RA, Nammalwar B. J. Heterocycl. Chem. 2011; 48: 991
- 5b Deng D, Guo H, Kang G, Ma L, He X, Ji B. CrystEngComm 2015; 17: 1871
- 5c Shi D, Rong L, Wang J, Zhuang Q, Wang X, Hu H. Tetrahedron Lett. 2003; 44: 3199
- 6 Su W, Yang B. Aust. J. Chem. 2002; 55: 695
- 7a Tang J, Li J, Zhang L, Ma S, Shi D, Zhang Q, Yang L, Wang X, Liu X, Liu C. J. Heterocycl. Chem. 2012; 49: 533
- 7b Wu X, Oschatz S, Block A, Spannenberg A, Langer P. Org. Biomol. Chem. 2014; 12: 1865
- 7c Tamaddon F, Pouramini F. Synlett 2014; 25: 1127
- 7d Chai H, Li J, Yang L, Liu M, Yang D, Zhang Q, Shi D. Chin. J. Chem. 2014; 32: 865
- 8a Narasimhulu M, Lee YR. Tetrahedron 2011; 67: 9627
- 8b Khaksar S, Gholami M. Res. Chem. Intermed. 2015; 41: 3709
- 8c Davoodnia A, Khashi M, Tavakoli-Hoseini N. Chin. J. Catal. 2014; 35: 1054
- 8d Wu J, Du X, Ma J, Zhang Y, Shi O, Luo L, Song B, Yang S, Hu D. Green Chem. 2014; 16: 3210
- 8e Tamaddon F, KazemiVarnamkhasti M. Carbohydr. Res. 2017; 437: 9
- 8f Deng D, Guo H, Ji B, Wang W, Ma L, Luo F. New J. Chem. 2017; 41: 12611
- 8g Tamaddon F, KazemiVarnamkhasti M. Synlett 2016; 27: 2510
- 8h Sharma R, Pandey AK, Chauhan PM. S. Synlett 2012; 23: 2209
- 8i Chen J, Su W, Wu H, Liu M, Jin C. Green Chem. 2007; 9: 972
- 9 Kumar M, Richa Richa, Sharma S, Bhatt V, Kumar N. Adv. Synth. Catal. 2015; 357: 2862
- 10a Zhou Y, Zhou H, Liu S, Pi D, Shen G. Tetrahedron 2017; 73: 3898
- 10b Chen D, Zhou Y, Liu S, Liu Q, Zhang K, Zhou H. Synlett 2018; 29: 1765
- 10c Pi D, Zhou H, Zhou Y, Liu Q, He R, Shen G, Uozumi Y. Tetrahedron 2018; 74: 2121
- 10d Chen Y, Liu S, Cui P, Zhang Y, Liu Q, Zhou H. Tetrahedron Lett. 2019; 60: 327
- 10e Zhou H, Sui Y, Jiang X, Yang B, Yu T. CN 108558778, 2018
- 11 Liu S, Zhou Y, Sui Y, Liu H, Zhou H. Org. Chem. Front. 2017; 4: 2175
- 12a Shen G, Zhou H, Du P, Liu S, Zou K, Uozumi Y. RSC Adv. 2015; 5: 85646
- 12b Shen G, Zhou H, Sui Y, Liu Q, Zou K. Tetrahedron Lett. 2016; 57: 587
- 13 2-Phenyl-2,3-dihydroquinazolin-4(1H)-one (3a); Typical Procedure A 10-mL tube was charged with 2-nitrobenzonitrile (1; 0.5 mmol), benzaldehyde (2a; 0.6 mmol), B2(OH)4 (2.5 mmol), CuCl (0.1 mmol), H2O (1 mL), and MeOH (1 mL), and the mixture was stirred at 60 °C for 3 h. The mixture was then extracted with EtOAc (3 × 5 mL) and the organic layers were combined, dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography [silica gel, PE–EtOAc (5:1)] to give a white solid; yield: 101.9 mg (91%); mp 224–225 °C. 1H NMR (400 MHz, CDCl3): δ = 7.99 (d, J = 7.2 Hz, 1 H), 7.66–7.63 (m, 2 H), 7.52–7.49 (m, 3 H), 7.39 (dt, J 1 = 7.6 Hz, J 2 = 1.6 Hz , 1 H), 6.95 (t, J = 7.6 Hz, 1 H), 6.72 (d, J = 8.0 Hz, 1 H), 5.95 (s, 1 H), 5.80 (s, 1 H), 4.44 (s, 1 H). 13C NMR (100 MHz, CDCl3): δ = 164.7, 147.2, 138.6, 134.0, 130.2, 129.2, 128.8, 127.4, 119.7, 115.7, 114.6, 69.1.