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

Abdolali Alizadeh; Rashid Ghanbaripour; Long-Guan Zhu

doi:10.1055/s-0033-1341202

Synlett, Table of Contents

Synlett 2014; 25(11): 1596-1600
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

Abdolali Alizadeh*

^aDepartment of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran Fax: +98(21)88006544 Email: abdol_alizad@yahoo.com Email: aalizadeh@modares.ac.ir

,

Rashid Ghanbaripour

^aDepartment of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran Fax: +98(21)88006544 Email: abdol_alizad@yahoo.com Email: aalizadeh@modares.ac.ir

,

Long-Guan Zhu

^bDepartment of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China

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Abstract

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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 system

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References

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 (C^4a of coumarin), 124.8 (CH of Ar), 127.2 (CH of Ar), 128.7 (CH of Ar), 131.0 (C^4a of quinazoline), 132.1 (CH of Ar), 133.5 (CH of Ar), 138.6 (CH⁴ of coumarin), 146.2 (C^8a of quinazoline), 152.7 (C^8a 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 (C^4a of coumarin), 119.8 (CH of Ar), 124.8 (CH of Ar), 127.2 (CH of Ar), 131.2 (C^4a of quinazoline), 133.5 (CH of Ar), 138.8 (CH⁴ of coumarin), 142.1 (C^8a of coumarin), 146.1 (C^8a 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

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