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
PDF herunterladen
Synlett 2014; 25(11): 1596-1600
DOI: 10.1055/s-0033-1341202
DOI: 10.1055/s-0033-1341202
letter
An Efficient Approach to the Synthesis of Coumarin-Bearing 2,3-Dihydro-4(1H)-Quinazolinone Derivatives Using a Piperidine and Molecular Iodine Dual-Catalyst System
Weitere Informationen
Publikationsverlauf
Received: 01. März 2014
Accepted: 22. März 2014
Publikationsdatum:
10. April 2014 (online)
Abstract
An efficient dual-catalyst system of piperidine and molecular iodine has been developed for the synthesis of 2-alkyl-2-(2-oxo-2H-chromen-3-yl)-2,3-dihydro-4(1H)quinazolinone derivatives by a four-component reaction of salicylaldehydes, β-keto esters, ammonium acetate, and isatoic anhydride. Good yields, mild reaction conditions, and easy purification are attractive features of the present method.
Key words
salicylaldehyde - β-keto ester - isatoic anhydride - ammonium acetate - 2-alkyl-2-(2-oxo-2H-chromen-3-yl)-2,3-dihydro-4(1H)quinazolinone - dual-catalyst systemSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References and Notes
- 1 Murray RD. H In Progress in the Chemistry of Organic Natural Products . Vol. 83. Herz W, Falk H, Kirby GW, Moore RE. Springer Verlag; Wien: 2002: 1-529
- 2 Murray RD. H, Mendez J, Brown SA. The Natural Coumarins: Occurrence, Chemistry and Biochemistry . John Wiley and Sons; New York: 1982: 21
- 3 Kontogiorgis C, Hadjipavlou-Litina D. J. Enzyme Inhib. Med. Chem. 2003; 18: 63
- 4a Cravotto G, Nano GM, Palmisano G, Tagliapietra S. Tetrahedron: Asymmetry 2001; 12: 707
- 4b Fan GJ, Mar W, Park MK, Wook Choi E, Kim K, Kim S. Bioorg. Med. Chem. Lett. 2001; 11: 2361
- 5 Kirkiacharian S, Thuy DT, Sicsic S, Bakhchinian R, Kurkjian R, Tonnaire T. Farmaco 2002; 57: 703
- 6a Cuzzocrea S, Mazzon E, Bevilaqua C, Constantino G, Britti D, Mazzullo G, De Sarro A, Caputi AP. Br. J. Pharmacol. 2000; 131: 1399
- 6b Kontogiorgis CA, Hadjipavlou-Litina DJ. J. Med. Chem. 2005; 48: 6400
- 7a Sayed HH, Shamroukh AH, Rashad AE. Acta Pharm. 2006; 56: 231
- 7b Sardari S, Mori Y, Horita K, Micetich RG, Nishibe S, Daneshtalab M. Bioorg. Med. Chem. 1999; 7: 1933
- 8 Kennedy RO, Zhorenes RD. Coumarins: Biology, Applications and Mode of Action . John Wiley and Sons; Chichester: 1997
- 9 Zabradnik M. The Production and Application of Fluorescent Brightening Agents. John Wiley and Sons; New York: 1992
- 10a Specht DP, Martic PA, Farid S. Tetrahedron 1982; 38: 1203
- 10b Williams JL. R, Specht DP, Farid S. Polym. Eng. Sci. 1983; 23: 1022
- 11 Piazzi L, Rampa A, Bisi A, Gobbi S, Belluti F, Cavalli A, Bartolini M, Andrisano V, Valenti P, Recanatini M. J. Med. Chem. 2003; 46: 2279
- 12 Opherk D, Schuler G, Waas W, Dietz R, Kubler W. Eur. Heart J. 1990; 11: 342
- 13 Cao YG, Liu XQ, Chen YC, Hao K, Wang GJ. Eur. J. Pharm. Sci. 2007; 30: 175
- 14a Majumdar KC, Samanta S, Ansary I, Roy B. RSC Advances 2012; 2: 2137
- 14b Katritzky AR, Ibrahim TS, Tala SR, Abo-Dya NE, Abdel-Samii ZK, El-Feky SA. Synthesis 2011; 1494
- 14c Moshkin VS, Sosnovskikh VY, Röschenthaler GV. Tetrahedron Lett. 2012; 53: 3568
- 14d Yoshioka E, Kohtani S, Miyabe H. Angew. Chem. Int. Ed. 2011; 50: 6638
- 14e Zhang G, Zhang Y, Yan J, Chen R, Wang S, Ma Y, Wang R. J. Org. Chem. 2012; 77: 878
- 14f Pal G, Paul S, Das AR. Synthesis 2013; 45: 1191
- 14g Karimi B, Khodabakhshi S, Eskandari K. Synlett 2013; 24: 998
- 14h Jafarpour F, Zarei S, Barzegar-Amiri Olia M, Jalalimanesh N, Rahiminejadan S. J. Org. Chem. 2013; 78: 2957
- 14i Wang Q, Finn MG. Org. Lett. 2000; 2: 4063
- 14j Petasis NA, Butkevich AN. J. Organomet. Chem. 2009; 694: 1747
- 14k Youn SW, Eom JI. Org. Lett. 2005; 7: 3355
- 14l Majumdar N, Korthals KA, Wulff WD. J. Am. Chem. Soc. 2012; 134: 1357
- 15a Michael JP. Nat. Prod. Rep. 2008; 25: 166
- 15b Rouffet M, de Oliveira CA. F, Udi Y, Agrawal A, Sagi I, McCammon JA, Cohen SM. J. Am. Chem. Soc. 2010; 132: 8232
- 15c Andrews S, Burgess SJ, Skaalrud D, Kelly JX, Peyton DH. J. Med. Chem. 2010; 53: 916
- 15d Lord AM, Mahon MF, Lloyd MD, Threadgill MD. J. Med. Chem. 2009; 52: 868
- 15e Behenna DC, Stockdill JL, Stoltz BM. Angew. Chem. 2008; 120: 2400
- 16 Noolvi MN, Patel HM, Bhardwaj V, Chauhan A. Eur. J. Med. Chem. 2011; 46: 2327
- 17 El-Helby AG. A, Wahab MH. A. Acta Pharm. 2003; 53: 127
- 18 Kabri Y, Azas N, Dumètre A, Hutter S, Laget M, Verhaghe P, Gellis A, Vanlee P. Eur. J. Med. Chem. 2010; 45: 616
- 19a Sadanadam YS, Reddy RM, Bhaskar A. Eur. J. Med. Chem. 1987; 22: 169
- 19b Bonola G, Sianesi E. J. Med. Chem. 1970; 13: 329
- 19c Hour ML, Huang L, Kuo S, Xia Y, Bastow K, Nakanishi Y, Hamel E, Lee K. J. Med. Chem. 2000; 43: 4479
- 20a Alanine A, Gobbi LC, Kolczewski S, Luebbers T, Peters JU, Steward L. US 2006293350 A1, 2006 ; Chem. Abstr. 2006, 146, 100721
- 20b Chaturvedula PV, Chen L, Civiello R, Degnan AP, Dubowchik GM, Han X, Jiang XJ, Macor JE, Poindexter GS, Tora GO, Luo G. US 2007149503 A1, 2007 ; Chem. Abstr. 2007, 147, 118256
- 20c Letourneau J, Riviello C, Ho KK, Chan JH, Ohlmeyer M, Jokiel P, Neagu I, Morphy JR, Napier SE. WO 2006095014 A1, 2006 ; Chem. Abstr. 2006, 145, 315012
- 21a Venkat Lingaiah B, Ezikiel G, Yakaiah T, Venkat Reddy G, Shanthan Rao P. Synlett 2006; 2507
- 21b Rostamizadeh S, Amani AM, Mahdavinia GH, Sepehrian H, Ebrahimi S. Synthesis 2010; 1356
- 21c Zhang Z.-H, Lü H.-Y, Yang S.-H, Gao J.-W. J. Comb. Chem. 2010; 12: 643
- 21d Khaksar S, Mohammadzadeh Talesh S. C. R. Chimie 2012; 15: 779
- 21e Yadav AK, Dhakad P, Ram Sharma G. Tetrahedron Lett. 2013; 54: 6061
- 21f Nelson AC, Kalinowski ES, Jacobson TL, Grundt P. Tetrahedron Lett. 2013; 54: 6804
- 22a Prudhvi Raju N, Jagan Mohan Reddy B, Anjibabu R, Muralikrishna K, Subba Reddy BV. Tetrahedron Lett. 2013; 54: 3639
- 22b Yusubov MS, Svitich DY, Yoshimura A, Nemykin VN, Zhdankin VV. Chem. Commun. 2013; 49: 11269
- 22c Rajendar K, Kant R, Narender T. Adv. Synth. Catal. 2013; 355: 3591
- 22d Rai P, Srivastava M, Singh J. RCS Adv. 2014; 4: 779
- 23a Wang XS, Yang K, Zhou J, Tu SJ. J. Comb. Chem. 2010; 12: 417
- 23b Lu L, Zhang MM, Jiang H, Wang XS. Tetrahedron Lett. 2013; 54: 757
- 24a Alizadeh A, Ghanbaripour R, Zhu LG. Synlett 2013; 24: 2124
- 24b Alizadeh A, Ghanbaripour R, Zhu LG. Synth. Commun. 2013; 43: 2575
- 24c Alizadeh A, Ghanbaripour R. Helv. Chim. Acta 2013; 96: 473
- 24d Alizadeh A, Saberi V, Mokhtari J. Synlett 2013; 24: 1825
- 24e Alizadeh A, Mokhtari J. Tetrahedron 2013; 69: 6313
- 24f Alizadeh A, Rezvanian A, Zhu LG. J. Org. Chem. 2012; 77: 4385
- 24g Alizadeh A, Ghanbaripour R, Zhu LG. Tetrahedron 2014; 70: 2048
- 25 To a solution of isatoic anhdyride (1 mmol) in DMF (2 mL) was added NH4OAc (1 mmol), and the solution was stirred for 15 min at 60 °C. Then, salicylaldehyde 1 (1 mmol), β-keto ester 2 (1 mmol), and piperidine (0.1 mmol) were added, and the solution was stirred. After 10 min molecular iodine (0.15 mmol) was added to the reaction mixture, and the reaction was stirred about 5 h. Upon completion (monitored by TLC) the solvent was evaporated under reduced pressure, and the residue was recrystallized from EtOH to afford the pure product 3a–h. 2-Methyl-2-(2-oxo-2H-chromen-3-yl)-2,3-dihydro-4(1H)quinazolinone (3a) White powder; 0.257 g, 84% yield; mp 298 °C (decomp.). IR (KBr): 3441 and 3169 (2 NH), 1717 (C=O), 1664 (CONH), 1609, 1570 and 1525 (Ar), 1199 (CO) cm–1. 1H NMR (400 MHz, DMSO-d 6): δ = 1.81 (s, 3 H, CH3), 6.65 (t, 3 J HH = 7.6 Hz, 1 H, CH of Ar), 6.86 (d, 3 J HH = 8.0 Hz, 1 H, CH of Ar), 7.18 (s, 1 H, NH), 7.24 (td, 3 J HH = 7.6 Hz, 4 J HH = 1.6 Hz, 1 H, CH of Ar), 7.33 (t, 3 J HH = 7.6 Hz, 1 H, CH of Ar), 7.39 (d, 3 J HH = 8.4 Hz, 1 H, CH of Ar), 7.56 (d, 3 J HH = 8.0 Hz, 1 H, CH of Ar), 7.60 (td, 3 J HH = 7.6 Hz, 4 J HH = 1.6 Hz, 1 H, CH of Ar), 7.73 (dd, 3 J HH = 7.6 Hz, 4 J HH = 1.2 Hz, 1 H, CH of Ar), 7.84 (1 H, s, CH4 of coumarin), 8.46 (s, 1 H, NH). 13C NMR (100 MHz, DMSO-d 6): δ = 26.5 (CH3), 69.2 (C2 of quinazoline), 114.1 (C3 of coumarin), 114.6 (CH of Ar), 115.9 (CH of Ar), 117.5 (CH of Ar), 118.0 (C4a of coumarin), 124.8 (CH of Ar), 127.2 (CH of Ar), 128.7 (CH of Ar), 131.0 (C4a of quinazoline), 132.1 (CH of Ar), 133.5 (CH of Ar), 138.6 (CH4 of coumarin), 146.2 (C8a of quinazoline), 152.7 (C8a of coumarin), 159.0 (CO2), 163.2 (CONH). MS: m/z = 264, 173, 145, 132, 118, 101, 89, 63. Anal. Calcd for C18H14N2O3: C, 70.58; H, 4.61; N, 9.15. Found: C, 70.81; H, 4.69; N, 8.99. 2-(8-Methoxy-2-oxo-2H-chromen-3-yl)-2-methyl-2,3-dihydro-4(1H)-quinazolinone (3b) Beige powder; 0.259 g, 77% yield; mp 247–249 °C. IR (KBr): 3345 and 3188 (2 NH), 1706 (C=O), 1650 (CONH), 1612 and 1478 (Ar), 1276 and 1184 (CO) cm–1. 1H NMR (400 MHz, DMSO-d 6): δ = 1.81 (s, 3 H, CH3), 3.88 (s, 3 H, OCH3), 6.65 (t, 3 J HH = 7.4 Hz, 1 H, CH of Ar), 6.85 (d, 3 J HH = 8.0 Hz, 1 H, CH of Ar), 7.17 (s, 1 H, NH), 7.24–7.29 (m, 4 H, CH of Ar), 7.56 (dd, 3 J HH = 7.8 Hz, 4 J HH = 1.4 Hz, 1 H, CH of Ar), 7.81 (s, 1 H, CH4 of coumarin), 8.44 (s, 1 H, NH). 13C NMR (100 MHz, DMSO-d 6): δ = 26.4 (CH3), 56.1 (OCH3), 69.2 (C2 of quinazoline), 114.1 (C3 of coumarin), 114.3 (CH of Ar), 114.6 (CH of Ar), 117.5 (CH of Ar), 118.6 (C4a of coumarin), 119.8 (CH of Ar), 124.8 (CH of Ar), 127.2 (CH of Ar), 131.2 (C4a of quinazoline), 133.5 (CH of Ar), 138.8 (CH4 of coumarin), 142.1 (C8a of coumarin), 146.1 (C8a of quinazoline), 146.2 (C ipso -OCH3), 158.7 (CO2), 163.2 (CONH). MS: m/z (%) = 336 (5) [M+], 321 (67), 161 (100), 120 (76), 92 (81), 76 (26), 65 (43). Anal. Calcd for C19H16N2O4: C, 67.85; H, 4.79; N, 8.33. Found: C, 77.69; H, 4.88; N, 8.21.
- 26 Frolova LV, Malik I, Uglinskii PY, Rogelj S, Kornienko A, Magedov IV. Tetrahedron Lett. 2011; 52: 6643