Synthesis and Crystal Structure of 2-(4-Oxo-3-o- tolyl-3,4-dihydroquinazolin-2-ylthio)acetohydrazide

Synthesis and Crystal Structure of 2-(4-Oxo-3-o- tolyl-3,4-dihydroquinazolin-2-ylthio)acetohydrazide

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摘要 The title compound was synthesized from 3-（2-methylphenyl）-2-thioxo-2,3-dihy- droquinazolin-4（1H）-one （4） which was prepared from 2-methylaniline in two steps. The structure was supported by the spectroscopic data and unambiguously confirmed by single-crystal X-ray diffraction studies. It crystallizes in the orthorhombic space group Pbca with unit cell dimensions a = 6.687（4）, b = 24.788（16）, c = 30.453（19） V = 5048（5） 3 and Z = 8. The title compound was synthesized from 3-（2-methylphenyl）-2-thioxo-2,3-dihy- droquinazolin-4（1H）-one （4） which was prepared from 2-methylaniline in two steps. The structure was supported by the spectroscopic data and unambiguously confirmed by single-crystal X-ray diffraction studies. It crystallizes in the orthorhombic space group Pbca with unit cell dimensions a = 6.687（4）, b = 24.788（16）, c = 30.453（19） V = 5048（5） 3 and Z = 8.

作者 Aamer Saeed Shams-ul-Mahmood Ulrich Flörke

机构地区 Department of Chemistry Department Chemie

出处《Chinese Journal of Structural Chemistry》 SCIE CAS CSCD 2012年第9期1329-1333,共5页 结构化学（英文）

基金 a research grant from the Higher Education Commission of Pakistan under project No. 4-279/PAK-US/HEC 2010-917

关键词 QUINAZOLINONE acetohydrazide SYNTHESIS quinazolinone, acetohydrazide, synthesis

分类号 O621.2 [理学—有机化学]

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1Mhaske, S. B.; Argade, N. P. The chemistry of recently isolated naturally occurring quinazolinone alkaloids. Tetrahedron 2006, 62, 9787–9826.
2Patel, B. N.; Patel, C. J. Synthesis and antimicrobial activity of 3-(1,3,4-oxadiazol-2-yl)quinazolin-4(3H)-ones. Sci Pharm. 2010, 78, 171–193.
3Bartroli, J.; Turmo, E.; Alguero, M.; Boncompte, E.; Vericat, M. L.; Conte, L.; Ramis, J.; Merlos, M.; Garcia-Rafanell, J.; Forn, J. Synthesis and antifungal activity of 3-substituted-4(3H)-quinazolinones. J. Med. Chem. 1998, 41, 1869–1882.
4Al-Obaid, A. M.; Abdel-Hamide , S. G.; El-Kashef, H. A.; Abdel-Aziz, A. A. M.; El-Azab, A. S.; Al-Khamees, H. A.; El-Subbagh. H. I. Substituted quinazolines, part 3. Synthesis, in vitro antitumor activity and molecular modeling study of certain 2-thieno-4(3H)-quinazolinone analogs. Eur. J. Med. Chem. 2009, 44, 2379–2391.
5Kamal, A.; Vijaya, B. E.; Janaki Ramaiah, M.; Dastagiri, D.; Surendranadha R. J.; Viswanath, A.; Sultana, F.; Pushpavalli, S. N. C. V. L.; Pal-Bhadra, M.; Srivastava, H. K.; Narahari, S. G.; Juvekar, A.; Sen, S.; Zingde, S. Quinazolinone linked pyrrolo[2, 1-c][1, 4]benzodiazepine (PBD) conjugates: design, synthesis and biological evaluation as potential anticancer agents. Bioorg. Med. Chem. 2010, 18, 526–542.
6Laddha, S. S.; Bhatnagar, P. S. A new therapeutic approach in Parkinson’s disease: some novel quinazoline derivatives as dual selective phosphor diesterase 1 inhibitors and anti-inflammatory agents. Bioorg. Med. Chem. 2009, 17, 6796–6802.
7G-khan-Kelek-i, N.; Koyunog-lu, S.; Yabanog-lu, S.; Yelek-i, K.; -zgen, -.; U-ar, G.; Erol, K.; Kendi, E.; Yesilada, A. New pyrazoline bearing 4(3H)-quinazolinone inhibitors of monoamine oxidase: synthesis, biological evaluation, and structural determinants of MAO-A and MAO-B selectivity Bioorg. Med. Chem. 2009, 17, 675–689.
8Mohsen, M. A.; Yahia, A. M.; Elkhairy, A. M.; Wahid, M. B.; Samir, Y. A. Synthesis of some new 4(3H)-quinazolinone-2-carboxaldehyde thiosemi carbazones and their metal complexes and a study on their anticonvulsant, analgesic, cytotoxic and antimicrobial activities - Part-1. Eur. J. Med. Chem. 2010, 45, 3365–3373.
9Abdel Gawad, N. M.; Georgey, H. H.; Youssef, R. M.; El Sayed, A. N. Design, synthesis, and anticonvulsant activity of novel quinazolinone analogues. Med. Chem. Res. 2011, 20, 1280–1286.
10Du, X.; Jiang, Y.; Qian, W.; Lu, X.; Walsh, J. P. Fatty acids inhibit growth-factor-induced diacylglycerol kinase an activation in vascular smooth-muscle cells. Biochem. J. 2001, 357, 275–282.

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2A.Bharathi,Selvaraj Mohana Roopan,Amir Kajbafvala,R.D.Padmaja,M.S.Darsana,G.Nandhini Kumari.Catalytic activity of TiO_2 nanoparticles in the synthesis of some2,3-disubstituted dihydroquinazolin-4(1H)-ones[J].Chinese Chemical Letters,2014,25(2):324-326. 被引量：1
3Qiu Qin He, Chao Mei Liu&Email:anrry_lcm@hotmail.com, Ke Li.First total synthesis of (±)-trolline[J].Chinese Chemical Letters,2007,18(6):651-652. 被引量：1
4Bin Wang,Zeng Li,Xiao Ning Wang,Jia Heng Tan,Lian Quan Gu,Zhi Shu Huang.A new approach to the facile synthesis of 2-substituted-quinazolin-4(3H)-ones[J].Chinese Chemical Letters,2011,22(8):951-953. 被引量：4
5SHIDa-Qing,RONGLiang-Ce,WANGJu-Xian,ZHUANGQi-Ya,WANGXiang-Shan,HUHong-Wen.Synthesis and Crystal Structure of 2,2-Pentamethylene-1,2,3,4-tetrahydroquinazolin-4-one[J].Chinese Journal of Structural Chemistry,2004,23(1):7-10.
6A.Davoodnia,S.Allameh,A.R.Fakhari,N.Tavakoli-Hoseini.Highly efficient solvent-free synthesis of quinazolin-4(3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones using tetrabutylammonium bromide as novel ionic liquid catalyst[J].Chinese Chemical Letters,2010,21(5):550-553. 被引量：8
7Syntheses of 2-Hydroxy-2H-pyrano[3,2-c]quinolin-5-ones from 4-Hydroxyquinilin-2-ones[J].厦门大学学报（自然科学版）,1999,38(S1):269-269.
8Youssef, Mohamed Salah K. Abbady, Mohamed S. Ahmed, Ragaa A. Omar, Ahmed A..Preparation and Reactions of 2-Methyl-7-（3-methyl-5-oxo-1- phenyl-2-pyrazolin-4-yl）-5-arylthiazolo[3,2-a]- pyrimido[4,5-d]oxazin-4（5H）-one[J].Chinese Journal of Chemistry,2011,29(7):1473-1482.
9Yong Jun GAO,Feng Jun LI,hi Shan JIANG(Department of Chemistry, Yanbian University, Yani, Jilin, 133002)Shi Chen ZHOU(Department of Chemistry, Jinzhou Teacher’s College, Jinzhou 121000).Synthesis of 1H-thiopyrano[3,4-b] Quinolin-4(3H)-one and TheirHeterocycle Fused Compounds[J].Chinese Chemical Letters,1997,8(1):5-6.
10M.Bakavoli,O.Sabzevari,M.Rahimizadeh.Microwave activated synthesis of 2-aryl-quinazolin-4(3H)ones[J].Chinese Chemical Letters,2007,18(12):1466-1468. 被引量：5

Chinese Journal of Structural Chemistry

2012年第9期

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Synthesis and Crystal Structure of 2-(4-Oxo-3-o- tolyl-3,4-dihydroquinazolin-2-ylthio)acetohydrazide

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