Synthesis of Cyclopenta[d]pyrimidinones and Hexahydroquinazolinones Catalyzed by Activated Carbon Supported Sulfuric Acid

doi:10.19894/j.issn.1000-0518.190334

Chinese Journal of Applied Chemistry ›› 2021, Vol. 38 ›› Issue (1): 44-50.DOI: 10.19894/j.issn.1000-0518.190334

• Full Papers • Previous Articles Next Articles

Synthesis of Cyclopenta[d]pyrimidinones and Hexahydroquinazolinones Catalyzed by Activated Carbon Supported Sulfuric Acid

REN Li-Lei^*, XIAO Li-Wei^*, LIU Guang-Xian, XU Ming-Ming

Faculty of Chemistry and Material Science, Langfang Normal University, Langfang 065000, China

Received:2019-12-13 Revised:2020-09-30 Published:2021-01-01 Online:2021-02-01
Supported by:
Educational Commission of Hebei Province (No.ZD2020153) and the Science and Technology of Langfang (No.2019011018)

Abstract

Abstract: An activated carbon supported sulfuric acid catalyst (H₂SO₄/AC) was prepared and characterized by Fourier transform infrared (FT-IR) spectrometry and X-ray diffraction (XRD). Various cyclopenta[d]pyrimidinones and hexahydroquinazolinones were synthesized by the reaction of aromatic aldehyde with urea and cyclopentone(cyclohexanone) catalyzed by H₂SO₄/AC in the absence of solvent. This method is simple and environmentally benign. The catalyst can be easily recovered and its activity maintains after being reused for 3 times.

Key words: Activated carbon supported sulfuric acid, Cyclopenta[d]pyrimidinones, Hexahydroquinazolinones, Multicomponent reactions

CLC Number:

O621.3

REN Li-Lei, XIAO Li-Wei, LIU Guang-Xian, XU Ming-Ming. Synthesis of Cyclopenta[d]pyrimidinones and Hexahydroquinazolinones Catalyzed by Activated Carbon Supported Sulfuric Acid[J]. Chinese Journal of Applied Chemistry, 2021, 38(1): 44-50.

References

[1] ATWAL K S, ROVNYAK G C, O'REILLY B C, et al. Substituted 1,4-dihydropyrimidines.3. synthesis of selectively functionalized 2-hetero-1,4-dihydropyrimidines[J]. J Org Chem, 1989, 54(25): 5898-5907.
[2] SAHER L, MAKHLOUFI-CHEBLI M, DERMECHE L, et al. Keggin and dawson-type polyoxometalates as effificient catalysts for the synthesis of 3,4-dihydropyrimidinones:experimental and theoretical studies[J]. Tetrahedron Lett, 2016, 57(13): 1492-1496.
[3] FAN W G, QUENEAU Y, POPOWYCZ F. HMF in multicomponent reactions: utilization of 5-hydroxymethylfurfural (HMF) in the Biginelli teaction[J]. Green Chem, 2018, 20(2): 485-492.
[4] EL-SUBBAGH H I, ABU-ZAID S M, MAHRAN M A, et al. Synthesis and biological evaluation of certain α,β-unsaturated ketones and their corresponding fused pyridines as antiviral and cytotoxic agents[J]. J Med Chem, 2000, 43(15): 2915-2921.
[5] ZHANG H H, ZHOU Z Q, YAO Z G, et al. Effificient synthesis of pyrimidinone derivatives by ytterbium chloride catalyzed Biginelli-type reaction under solvent-free conditions[J]. Tetrahedron Lett, 2009, 50(14): 1622-1624.
[6] NARASASHETTY J, KALEGOWDA S. Biginelli reaction of vicinal diols: a new route for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives[J]. Lett Org Chem, 2017, 14(5): 330-336.
[7] LIU M L, SHU M M, YAO C C, et al. Synthesis of pyrido-fused quinazolinone derivatives via copper-catalyzed domino reaction[J]. Org Lett, 2016, 18(4): 824-827.
[8] SELVAM T P, KUMAR P V, KUMAR A S, et al. Study of inhibitory mechanism and binding mode of the thiazolo quinazoline compounds to HIV-1 integrase by docking[J]. J Pharm Res, 2010, 3(7): 1637-1647.
[9] WEI L S, HE G X, KONG X F, et al. Gold(III)-catalyzed selective cyclization of alkynyl quinazolinone-tethered pyrroles: synthesis of fused quinazolinone scaffffolds[J]. J Org Chem, 2018, 83(12): 6719-6727.
[10] WU Y L, CHENG Y, ZHOU X D, et al. Dacomitinib versus gefitinib as first-line treatment for patients with EGFR-mutation-positive non-small-cell lung cancer (ARCHER 1050): a randomised, open-label, phase 3 trial[J]. Lancet Oncol, 2017, 18(11): 1454-1466.
[11] ANTIPENKO L, KARPENKO A, KOVALENKO S, et al. Synthesis of new 2-thio-[1,2,4]triazolo[1,5-c]quinazoline derivatives and its antimicrobial activity[J]. Chem Pharm Bull, 2009, 57(6): 580-585.
[12] ELGEMEIE G E H, ATTIA A M E, ALKABAI S S. Nucleic acid components and their analogues: new synthesis of bicyclic thiopyrimidine nucleosides[J]. Nucleosides Nucleotides Nucl Acids, 2000, 19(4): 723-733.
[13] ZHU Y L, HUANG S L, PAN Y J. Highly chemoselective multicomponent Biginelli-type condensations of cycloalkanones, urea or thiourea and aldehydes[J]. Eur J Org Chem, 2005, 2005(11): 2354-2367.
[14] GHASHANG M, MANSOOR S S, ASWIN K. An efficient and environmentally friendly procedure for the synthesis of some novel 8-benzylidene-4-phenyl-3,4,5,6,7,8-hexahydro-1H-quinazolin-2-ones/thiones using tetrabutylammonium hexatungstate as a reusable heterogeneous catalyst under solvent-free conditions[J]. Bull Korean Chem Soc, 2013, 34(11): 3289-3294.
[15] ZHOU Z L, WANG P C, LU M. Bronsted acidic ionic liquid [C₃SO₃HDoim]HSO₄ catalyzed one-pot three-component Biginelli-type reaction: an effificient and solvent-free synthesis of pyrimidinone derivatives and its mechanistic study[J]. Chinese Chem Lett, 2016, 27(2): 226-230.
[16] HOTE B S, MANDAWAD G G, PATIL S G. Cyanuric chloride catalyzed three component, one-pot synthesis of Biginelli-type pyrimidinone derivatives[J]. Polycyclic Aromat Compd, 2019, 39: 1-7.
[17] HAJIPOUR A R, GHAYEB Y, SHEIKHAN N. Bronsted acidic ionic liquid as an efficient and reusable catalyst for one-pot, three-component synthesis of pyrimidinone derivatives via Biginelli-type reaction under solvent-free conditions[J]. Synth Commun, 2011, 41(15):2226-2233.
[18] LEI M, MA L, HU L H. An effificient and environmentally friendly procedure for synthesis of pyrimidinone derivatives by use of a Biginelli-type reaction[J]. Monatsh Chem, 2010, 141: 1005-1008.
[19] 肖立伟, 高红杰, 任丽磊, 等. 改性活性炭负载氯化铁催化氧杂蒽衍生物的合成[J]. 应用化学, 2015, 32(3): 304-309.
   XIAO L W, GAO H J, REN L L, et al. Synthesis of xanthene derivatives catalyzed by modified active carbon supported ferric chloride[J]. Chinese J Appl Chem, 2015, 32(3): 304-309.
[20] 李晓微, 许海芬, 周晋, 等. 氮掺杂碳材料负载Pd纳米催化剂在有机反应中的最新研究进展[J]. 有机化学, 2018, 38(8): 1917-1929.
   LI X W,XU H F, ZHOU J, et al. Recent progress of N-doped carbon materials supported Pd nanocatalysts in organic reactions[J]. Chinese J Org Chem,2018, 38(8):1917-1929.
[21] 吴丹, 周聪, 赵素英. 负载型烯烃氢甲酰化反应催化剂研究进展[J]. 化工进展, 2019, 38(10): 4542-4553.
   WU D, ZHOU C, ZHAO S Y. Research progress of immobilized catalysts for olefin hydroformylation[J]. Chem Ind Eng Pro, 2019, 38(10): 4542-4553.
[22] 郑昌武, 柴卓, 赵刚. 高分子负载催化剂的设计、合成及其在有机合成反应中的应用[J]. 化学进展, 2010, 22(7): 1442-1456.
   ZHENG C W, CHAI Z, ZHAO G. Polymer-supported catalysts designing, synthesis and their application on organic synthetic reaction[J]. Prog Chem, 2010, 22(7): 1442-1456.
[23] DILMAGHANI K A, ZEYNIZADEH B, PARASAJAM H. The efficient synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and their sulfur derivatives with H₂SO₄ immobilized on activated charcoal[J]. Phosphorus Sulfur Silicon Relat Elem, 2012, 187: 544-553.
[24] 马峰, 李立强, 郝海娥, 等. 无溶剂条件下活性炭固载硫酸催化酮和芳香醛的Cross-Aldol 缩合反应[J]. 有机化学, 2010, 30(3): 419-423.
   MA F, LI L Q, HAO H E, et al. Activated carbon supported sulfuric acid as an efficient catalyst for cross-aldol condensation of ketones with aromatic aldehydes under solvent-free conditions[J]. Chinese J Org Chem, 2010, 30(3): 419-423.
[25] 葛恬, 宋洁, 姚志刚, 等. 三氯化铁催化Biginelli型反应合成芳亚甲基稠环嘧啶酮[J]. 有机化学, 2015, 35(7): 1570-1575.
   GE T, SONG J, YAO Z G, et al. Efficient synthesis of arylidene heterobicyclic pyrimidinone via ferric chloride catalyzed Biginelli-type reaction[J]. Chinese J Org Chem, 2015, 35(7): 1570-1575.
[26] El-SAGHIER A M M, AHMED E A, MAHMOUD A M A. Rapid and green chemistry catalysis in synthesis of hexahydroquinazolinones and cyclopenta, cyclohepta[d]pyrimidinones with prediction of biological activity via PASS INET[J]. J Pharm Appl Chem, 2015, 1(1): 9-19.
[27] 陈晓玲, 陈静雯, 鲍宗必, 等. MIL-101(Cr)-SO₃H 催化2-取代喹啉衍生物转移氢化反应的研究有机化学[J]. 有机化学, 2019, 39(6): 1681-1687.
   CHEN X L, CHEN J W, BAO Z B, et al. MIL-101(Cr)-SO₃H catalyzed transfer hydrogenation of 2-substituted quinoline derivatives[J]. Chinese J Org Chem, 2019, 39(6): 1681-1687.

Synthesis of Cyclopenta[d]pyrimidinones and Hexahydroquinazolinones Catalyzed by Activated Carbon Supported Sulfuric Acid

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Min-Xiao XU, Liang WANG, Cheng-Fang CHEN. Rongalite Promoted Arylation of Benzoquinone [J]. Chinese Journal of Applied Chemistry, 2023, 40(3): 413-419.
[2]	ZHANG Tianyi, NIAN Wenxia, JIN Ying . Organocatalytic Asymmetric Michael Addition of Anthrone with β-Nitroolefins [J]. Chinese Journal of Applied Chemistry, 2015, 32(4): 422-427.
[3]	TANG Nana,LIU Leifang . Research Progress in Suzuki Coupling Reaction of Potassium Organotrifluoroborates [J]. Chinese Journal of Applied Chemistry, 2015, 32(1): 10-18.
[4]	YAO Yuanyong1,2, WU Lanyan1, SHU Hua1, TANG Bangcheng1, XUE Wei2. Synthesis of α-Aminophosphonates by Bronsted Acid Catalysis [J]. Chinese Journal of Applied Chemistry, 2014, 31(12): 1428-1433.
[5]	ZHOU Weijie, SUN Xiaoqiang, XI Haitao*. Synthesis and Fluorescence Properties of Hyaluronic Acid Derivatives Containing Fluorinated Coumarin [J]. Chinese Journal of Applied Chemistry, 2014, 31(08): 916-921.
[6]	YIN Zhigang*, GUO Haiyan, QIAN Hengyu, ZHANG Tongyan, QIN Jinwan, ZHANG Yingjun. Synthesis and Application of a Special Colorant Used in Preparing Yellow Polyurethane Elastic Membrane [J]. Chinese Journal of Applied Chemistry, 2014, 31(08): 901-910.
[7]	ZENG Wei, CHEN Fuxue*. Recent Advances in Radical Trifluoromethylation Reactions [J]. Chinese Journal of Applied Chemistry, 2014, 31(06): 627-641.
[8]	XIAO Liwei*, KONG jie, ZHOU Qiuxiang, HU Yueli. One Pot Synthesis of β-Amino Ketone Derivatives Catalyzed by Polystyrene-supported Ferric Chloride [J]. Chinese Journal of Applied Chemistry, 2014, 31(06): 715-720.
[9]	KE Fang1*, WU Wen2, LI Peng1, LIN Chen1. Microwave-assisted Synthesis of Benzothiazole Derivatives in Aqueous Solution [J]. Chinese Journal of Applied Chemistry, 2014, 31(06): 721-725.
[10]	FENG Cuilan*, XU Haiyun, LIU Lantao, WANG Jing, LIU Ying. Catalytic Synthesis of Diaryl Ethers with Magnetically Recoverable Fe₃O₄ Nanoparticles Under Solvent-free and Ligand-free Conditions [J]. Chinese Journal of Applied Chemistry, 2014, 31(05): 536-540.
[11]	ZHAO Xuejing, ZHU Jie, LU Ming*. Improvement of the Oxidation Process in the Synthesis of 2,6-Diamino-3,5-dinitropyrazine-1-oxide [J]. Chinese Journal of Applied Chemistry, 2014, 31(01): 41-49.
[12]	DUAN Zhifang, LI Chongbi*, WU Xufang, CHEN Gang. Solid Phase Grinding Synthesis and Plant Growth Activities of Arylureido-acylthiourea Derivatives [J]. Chinese Journal of Applied Chemistry, 2013, 30(12): 1429-1433.
[13]	LI Yanqin1*, YU Fengli2, ZHUANG Shengli1. Improved Synthetic Method and Characterization of Emedastine Difumarate [J]. Chinese Journal of Applied Chemistry, 2013, 30(11): 1285-1288.
[14]	ZHANG Feng1, FANG Zheng1, LI Xiaolin1, HE Wei1, YUAN Aibang2, GUO Kai2*. Applications of Ugi Reaction to the Synthesis of Natural Products [J]. Chinese Journal of Applied Chemistry, 2013, 30(11): 1237-1249.
[15]	GUO Wenyan1,2, CHEN Jianxin1*. A New Method for Synthesizing α-Aminoamide Compounds [J]. Chinese Journal of Applied Chemistry, 2013, 30(10): 1114-1119.