A Solvent-Free 2-Chloro-1-methylpyridinium Iodide (CMPI)-Mediated Biginelli Reaction for the Construction of 3,4-Dihydropyrimidin-2(1H)-ones/thiones

Ashish Kumar; Shashi Pandey; Monika Gupta; Chatrasal S. Rajput

doi:10.1055/a-2508-9681

Synthesis, Inhaltsverzeichnis

Synthesis 2025; 57(07): 1329-1338
DOI: 10.1055/a-2508-9681

paper

A Solvent-Free 2-Chloro-1-methylpyridinium Iodide (CMPI)-Mediated Biginelli Reaction for the Construction of 3,4-Dihydropyrimidin-2(1H)-ones/thiones

Ashish Kumar

^aSchool of Basic Sciences, Department of Chemistry, Babu Banarasi Das University, Lucknow, Uttar Pradesh 226028, India

^bChemistry Innovation Research Center, Jubilant Biosys Ltd, Greater Noida, Uttar Pradesh 201310, India

,

Shashi Pandey

^cDepartment of Chemistry, Faculty of Science, University of Lucknow, Lucknow, Uttar Pradesh 226007, India

,

Monika Gupta

^aSchool of Basic Sciences, Department of Chemistry, Babu Banarasi Das University, Lucknow, Uttar Pradesh 226028, India

,

Chatrasal S. Rajput

^bChemistry Innovation Research Center, Jubilant Biosys Ltd, Greater Noida, Uttar Pradesh 201310, India

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

The Biginelli product dihydropyrimidinones (DHPMs) and their derivatives have enormous biological significance. This article describes the exploration of 2-chloro-1-methylpyridinium iodide (CMPI) reagent for the development of an environmentally safe, solvent-free protocol to construct the functionalized 3,4-dihydropyrimidin-2(1H)-ones/thiones. The protocol involves the three-component condensation reaction of β-keto ester, aldehyde, and urea or thiourea at elevated temperature. The key advantages of the protocol are its capacity to provide both environmental and economic benefits owing to its solvent-free conditions, short reaction times, simple workup, and good to excellent isolated yield of DHPMs.

Keywords

Biginelli reaction - CMPI - 3,4-dihydropyrimidin-2(1H)-ones/thiones (DHPMs) - one-pot condensation - tri-component reaction

Volltext

Referenzen

References
1 Atwal KS, Swanson BN, Unger SE, Floyd DM, Moreland S, Hedberg A, O’Reilly BC. J. Med. Chem. 1991; 34: 806
2 Fu NY, Yuan YF, Cao Z, Wang SW, Wang JT, Peppe C. Tetrahedron 2002; 58: 4801
3 Sujatha K, Shanmugam P, Perumal PT, Muralidharan D, Rajendran M. Bioorg. Med. Chem. Lett. 2006; 16: 4893
4 Wisén S, Androsavich J, Evans CG, Chang L, Gestwicki JE. Bioorg. Med. Chem. Lett. 2008; 18: 60
5 Marich YA, Al-Salihi NJ, Al-Masoudi NA. Eur. J. Chem. 2014; 588
6 Wu W, Chen M, Wang R, Tu H, Yang M, Ouyang G. Chem. Pap. 2019; 73: 719
7 Farghaly TA, Harras MF, Alsaedi AM. R, Thakir HA, Mahmoud HK, Katowah DF. Mini Rev. Med. Chem. 2023; 23: 821
8 Ahmed K, Choudhary MI, Saleem RS. Z. Eur. J. Med. Chem. 2023; 259: 115701
9 Kostova I, Atanasov PY. Curr. Org. Chem. 2017; 21: 2096
10 Rashid HU, Martines MA. U, Duarte AP, Jorge J, Rasool S, Muhammad R, Umar MN. RSC Adv. 2021; 11: 6060
11 Bahekar SS, Shinde DB. Bioorg. Med. Chem. Lett. 2004; 14: 1733
12 Oliver CK. Tetrahedron 1993; 49: 6937
13 Folkers K, Harwood HJ, Johnson TB. J. Am. Chem. Soc. 1932; 54: 3751
14 Gupta R, Gupta AK, Paul S, Kachroo PL. Indian J. Chem. 1995; 34B: 151
15 Bose AK, Manhas MS, Pednekar S, Ganguly SN, Dang H, He W, Mandadi A. Tetrahedron Lett. 2005; 46: 1901
16 Salehi P, Dabiri M, Zolfigol MA, Bodaghi Fard MA. Tetrahedron Lett. 2003; 44: 2889
17 Shen ZL, Xu XP, Ji SJ. J. Org. Chem. 2010; 75: 1162
18 Bose DS, Fatima L, Mereyala HB. J. Org. Chem. 2003; 68: 587
19 Ramos LM, Ponce de Leon y Tobio AY, dos Santos MR, de Oliveira HC. B, Gomes AF, Gozzo FC, Neto BA. D. J. Org. Chem. 2012; 77: 10184
20 Kappe CO, Falsone SF. Synlett 1998; 718
21 Lu J, Ma H. Synlett 2000; 63
22 Lu J, Bai Y. Synthesis 2002; 466
23 Yadav JS, Reddy BV. S, Srinivas R, Venugopal C, Ramalingam T. Synthesis 2001; 1341
24 Zhang H, Hu Q, Liu J, Zhang P, Fu S, Wu S. ACS Appl. Nano Mater. 2022; 5: 16987
25 Oboudatian HS, Naeimi H, Moradian M. RSC Adv. 2021; 11: 7271
26 Heravi MM, Ghavidel M, Heidari B. Curr. Org. Synth. 2016; 13: 569
27 Desai B, Dallinger D, Kappe CO. Tetrahedron 2006; 62: 4651
28 Roy SR, Jadhavar PS, Seth K, Sharma KK, Chakraborti AK. Synthesis 2011; 2261
29 Ma Y, Qian C, Wang L, Yang M. J. Org. Chem. 2000; 65: 3864
30 Wang R, Liu Z-Q. J. Org. Chem. 2012; 77: 3952
31 Guo Y, Tang H, Gao Z, Meng X, Yu H, Zhong H, Huang G, Zou C. ChemistrySelect 2017; 2: 8253
32 Yamano Y, Tsuboi K, Hozaki Y, Takahashi K, Jin XH, Ueda N, Wada A. Bioorg. Med. Chem. 2012; 20: 3658
33 Mukaiyama T, Usui M, Saigo K. Chem. Lett. 1976; 5: 49
34 Kulikov OV, Incarvito C, Hamilton AD. Tetrahedron Lett. 2011; 52: 3705
35 Salarinejad S, Islami MR, Abbasnejad M, Zigheimat F, Kooshki R, Pouramiri B, Hosseini FS. Chemistry Select 2020; 5: 14190
36 Huang H, Iwasawa N, Mukaiyama T. Chem. Lett. 1984; 13: 1465
37 Chen L, Luo G. Tetrahedron Lett. 2019; 60: 268
38 Qi D, Dong W, Peng Z, Zhang Y, An D. Tetrahedron 2019; 75: 130427
39 Rajput CS, Srivastava S, Kumar A, Pathak A. Tetrahedron Lett. 2021; 65: 152791
40 Pandey RK, Gupta M, Rajput CS, Singh AS. ARKIVOC 2023; (vii): 202312042
41 Tocco G, Laus A, Caboni P. Tetrahedron Lett. 2022; 104: 154045
42 Ghonchepour E, Islami MR, Nejadshafiee V. Lett. Org. Chem. 2023; 20: 837
43 Kumar A, Pandey S, Gupta M, Rajput CS. Tetrahedron 2024; 167: 134248
44 Pandey S, Kushwaha P. Tetrahedron 2024; 161: 134067
45 Pandey S, Khan S, Singh A, Gauniyal HM, Kumar B, Chauhan PM. S. J. Org. Chem. 2012; 77: 10211
46 Singh D, Pandey S, Chouhan PS, Kant R, Chauhan PM. S. ChemistrySelect 2016; 5: 6780
47 Alizadeh A, Rostamnia S. Synthesis 2010; 4057
48 Elhamifar D, Shabani A. Eur. J. Chem. 2014; 3212
49 Nath J, Chaudhuri MK. Synth. Commun. 2010; 40: 2976
50 Kaur K, Knaus EE. J. Heterocycl. Chem 2007; 44: 669
51 Boumoud T, Boumoud B, Mosset P, Debache A. Eur. J. Chem. 2011; 312
52 Azarifar D, Badalkhani O, Abbasi Y. J. Sulfur Chem. 2016; 37: 1
53 Ali F, Khan KM, Salar U, Iqbal S, Taha M, Ismail NH, Ali B. Bioorg. Med. Chem. 2016; 24: 3624
54 Xia M, Wang Y. Synthesis 2003; 262
55 Singh V, Kaur S, Ratti R, Kad GL, Singh J. Indian J. Chem. 2010; 49B: 611
56 Ramalingan C, Kwak YW. Tetrahedron 2008; 64: 5023
57 Karimi B, Mobaraki A, Mirzaei HM, Zareyee D, Vali H. ChemCatChem 2013; 6: 212
58 Kumar TD. A, Swathi N, Subrahmanyam CV. S, SatyaNarayana K. Lett. Org. Chem. 2021; 18: 520
59 Ertan M, Balkan A, Saraç S, Uma S, Renaud JF, Rollad Y. Arch. Pharm. (Weinheim) 1991; 324: 135
60 Guo Y, Tang H, Gao Z, Meng X, Yu H, Zhong H, Huang G, Zou C. ChemistrySelect 2017; 2: 8253
61 Shirini F, Zolfigol MA, Mollarazi E. Synth. Commun. 2006; 36: 2307

Zusatzmaterial

Supporting Information