活性炭负载硫酸催化合成环戊并[d]嘧啶酮和六氢喹唑啉酮

任丽磊 肖立伟 刘光仙 徐明明

引用本文: 任丽磊, 肖立伟, 刘光仙, 徐明明. 活性炭负载硫酸催化合成环戊并[d]嘧啶酮和六氢喹唑啉酮[J]. 应用化学, 2021, 38(1): 44-50. doi: 10.19894/j.issn.1000-0518.190334 shu
Citation:  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. doi: 10.19894/j.issn.1000-0518.190334 shu

活性炭负载硫酸催化合成环戊并[d]嘧啶酮和六氢喹唑啉酮

    通讯作者: 任丽磊,E-mail:renll1409@163.com; 肖立伟,E-mail:xiaoliwei2000@sina.com
  • 基金项目:

    河北省教育厅重点项目(No.ZD2020153)和廊坊市科技局经费自筹项目(No.2019011018)资助

摘要: 制备了一种活性炭负载硫酸催化剂(H2SO4/AC),利用傅里叶变换红外光谱仪(FT-IR)和X射线衍射仪(XRD)表征了其形貌。在该催化剂作用下,以芳醛、尿素、环戊酮(环己酮)为原料,在无溶剂条件下经三组分一锅法反应合成了系列环戊并[d]嘧啶酮(六氢喹唑啉酮)。该方法用于合成此两类化合物操作简单,对环境友好,具有良好的应用前景。催化剂易于回收和循环使用,可重复使用3次,仍保持较高活性。

English


    1. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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.

  • 加载中
计量
  • PDF下载量:  0
  • 文章访问数:  23
  • HTML全文浏览量:  0
文章相关
  • 收稿日期:  2019-12-13
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

/

返回文章