- Recyclable palladium-catalyzed carbonylative annulation of 2-iodoanilines with acid anhydrides: A practical synthesis of 2-alkylbenzoxazinones
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A highly efficient heterogeneous palladium-catalyzed carbonylative annulation of 2-iodoanilines and acid anhydrides has been developed. The reaction proceeds effectively in toluene using N,N-diisopropylethylamine (DiPEA) as the base at 100 °C under 2 bar of CO and provides a novel, general, and practical method for the assembly of a wide variety of 2-alkylbenzoxazinones with high functional group tolerance and good to excellent yields. This supported palladium complex can be readily separated from the product and recovered by a simple filtration of the reaction solution and reused up to seven times with almost consistent catalytic efficiency.
- Zhou, Zebiao,Huang, Bin,Cai, Mingzhong
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p. 3150 - 3163
(2021/08/30)
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- Design, Synthesis, and Structure-Activity Relationship of Quinazolinone Derivatives as Potential Fungicides
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Plant diseases caused by phytopathogenic fungi reduce the yield and quality of crops. To develop novel antifungal agents, we designed and synthesized eight series of quinazolinone derivatives and evaluated their anti-phytopathogenic fungal activity. The bioassay results revealed that compounds KZL-15, KZL-22, 5b, 6b, 6c, 8e, and 8f exhibited remarkable antifungal activity in vitro. Especially, compound 6c displayed the highest bioactivity against Sclerotinia sclerotiorum, Pellicularia sasakii, Fusarium graminearum, and Fusarium oxysporum, displaying appreciable IC50 values (50% inhibitory concentration) of 2.46, 2.94, 6.03, and 11.9 μg/mL, respectively. A further mechanism interrogation revealed abnormal mycelia, damaged organelles, and changed permeability of cell membranes in S. sclerotiorum treated with compound 6c. In addition, the in vivo bioassay indicated that compound 6c possessed comparable curative and protective effects (87.3 and 90.7%, respectively) to the positive control azoxystrobin (89.5 and 91.2%, respectively) at 100 μg/mL concentration against S. sclerotiorum. This work validated the potential of compound 6c as a new and promising fungicide candidate, contributing to the exploration of potent antifungal agents.
- Peng, Jing-Wen,Yin, Xiao-Dan,Li, Hu,Ma, Kun-Yuan,Zhang, Zhi-Jun,Zhou, Rui,Wang, Yu-Ling,Hu, Guan-Fang,Liu, Ying-Qian
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p. 4604 - 4614
(2021/05/06)
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- One-Pot Synthesis of Trifluoromethylated Quinazolin-4(3 H)-ones with Trifluoroacetic Acid as CF3 Source
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A novel and convenient one-pot sequential cascade method for the preparation of 2-trifluoromethylquinazolin-4(3H)-ones is described. Trifluoroacetic acid (TFA) was employed as inexpensive and readily available CF3 source, which in the presence
- Almeida, Sofia,Marti, Roger,Vanoli, Ennio,Abele, Stefan,Tortoioli, Simone
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p. 5104 - 5113
(2018/05/22)
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- Enantioselective Synthesis of 3-Arylquinazolin-4(3H)-ones via Peptide-Catalyzed Atroposelective Bromination
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We report the development of a tertiary amine-containing β-turn peptide that catalyzes the atroposelective bromination of pharmaceutically relevant 3-arylquinazolin-4(3H)-ones (quinazolinones) with high levels of enantioinduction over a broad substrate scope. The structure of the free catalyst and the peptide-substrate complex were explored using X-ray crystallography and 2D-NOESY experiments. Quinazolinone rotational barriers about the chiral anilide axis were also studied using density functional theory calculations and are discussed in light of the high enantioselectivities observed. Mechanistic studies also suggest that the initial bromination event is stereodetermining, and the major monobromide intermediate is an atropisomerically stable, mono-ortho-substituted isomer. The observation of stereoisomerically stable monobromides stimulated the conversion of the tribromide products to other atropisomerically defined products of interest. For example, (1) a dehalogenation Suzuki-Miyaura cross-coupling sequence delivers ortho-arylated derivatives, and (2) a regioselective Buchwald-Hartwig amination procedure installs para-amine functionality. Stereochemical information was retained during these subsequent transformations.
- Diener, Matthew E.,Metrano, Anthony J.,Kusano, Shuhei,Miller, Scott J.
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supporting information
p. 12369 - 12377
(2015/10/12)
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- Optimization of rutaecarpine as ABCA1 up-regulator for treating atherosclerosis
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ATP-binding cassette transporter A1 (ABCA1) is a key transporter and receptor in promoting cholesterol efflux, and increasing the expression level of ABCA1 is antiatherogenic. In our previous study, rutaecarpine (RUT) was found to protect ApoE-/- mice from developing atherosclerosis through preferentially up-regulating ABCA1 expression. In the present work, a series of RUT derivatives were synthesized and examined as ABCA1 expression up-regulators. Compounds CD1, CD6, and BCD1-2 were found to possess the most potential activity as antiatherosclerotic agents among all compounds tested.
- Li, Yongzhen,Feng, Tingting,Liu, Peng,Liu, Chang,Wang, Xiao,Li, Dongsheng,Li, Ni,Chen, Minghua,Xu, Yanni,Si, Shuyi
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supporting information
p. 884 - 888
(2014/09/17)
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- Palladium-catalyzed carbonylative synthesis of benzoxazinones from N -(o -bromoaryl)amides using paraformaldehyde as the carbonyl source
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Carbonylation reactions have been widely used in organic synthesis. However, the manipulation of toxic and pressurized carbon monoxide limited their applications in organic laboratories. The search for alternative carbonyl sources as an important method for carbonylative organic synthesis is spreading. Herein, a series of substituted benzoxazinones were synthesized from N-(o-bromoaryl)amides by palladium-catalyzed carbonylation with paraformaldehyde as the carbonyl source, which is inexpensive, stable, and easy to use. Notably, this is the first example of using paraformaldehyde as the CO source in palladium-catalyzed carbonylative synthesis of heterocycles.
- Li, Wanfang,Wu, Xiao-Feng
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p. 10410 - 10416
(2015/02/19)
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- A general palladium-catalyzed carbonylative synthesis of 2-alkylbenzoxazinones from 2-bromoanilines and acid anhydrides
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(C), its (O)K! An efficient palladium-catalyzed carbonylative synthesis of 2-alkylbenzoxazinones has been developed (see scheme). By starting from 2-bromoanilines and acid anhydrides, the corresponding products were isolated in good yields. Copyright
- Wu, Xiao-Feng,Neumann, Helfried,Beller, Matthias
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supporting information
p. 12599 - 12602
(2012/11/07)
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- The stereodivergent aziridination of allylic carbamates, amides and sulfonamides
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A stereodivergent protocol for the aziridination of a range of cyclic allylic amine derivatives has been developed. syn-Products can be obtained in >99:1 dr under H-bonded control and anti-products are obtained in >99:1 dr under steric control by judiciou
- Davies, Stephen G.,Ling, Kenneth B.,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.,Woods, Philip A.
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experimental part
p. 6806 - 6813
(2010/09/17)
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- Synthesis leading to novel 2,4,6-trisubstituted quinazoline derivatives, their antibacterial and cytotoxic activity against thp-1, hl-60 and a375 cell lines
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A series of novel 2,4,6-trisubstituted quinazoline derivatives 6 have been synthesized from anthranilic acids 1 in five steps via benzoxazinones 2, N-benzoyl benzamides 3, quinazol-4-ones 4, 4-chloroquinazolines 5. Products 6 have been screened for antibacterial and cytotoxic activity, promising compounds have been identified.
- Chandrika, P Mani,Yakaiah,Narsaiah,Sridhar,Venugopal,Rao, J Venkateshwara,Kumar, K Pranay,Murthy,Rao, A Raghu Ram
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scheme or table
p. 840 - 847
(2009/12/24)
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- Synthesis and cytotoxic activity of novel quinazolino-β-carboline-5- one derivatives
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A novel series of quinazolino-β-carbolinone derivatives was synthesized and evaluated for their in vitro and in vivo anticancer activity. Many compounds have shown good in vitro activity in the range 1-8μM concentration. Three of the compounds were further tested in nude mice bearing HT-29 colon cancer xenografts.
- Baruah, Bipul,Dasu, Kavitha,Vaitilingam, Balasubramanian,Mamnoor, Premkumar,Venkata, Prasanthi Penubaka,Rajagopal, Sriram,Yeleswarapu, Koteswar Rao
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p. 1991 - 1994
(2007/10/03)
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- The design and synthesis of novel orally active inhibitors of AP-1 and NF-κB mediated transcriptional activation. SAR of in vitro and in vivo studies
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We have developed novel orally active quinazoline analogues as inhibitors of AP-1 and NF-κB mediated transcriptional activation. Among the derivatives prepared, 1-[2-(2-thienyl)quinazolin-4-ylamino]-3-methyl-3- pyrroline-2,5-dione (10) showed significant activity in an adjuvant-induced arthritis rat model by reducing the swelling by 65% in the non-injected foot. The synthesis, structure-activity relationship, and in vivo activity are described.
- Palanki, Moorthy S. S.,Erdman, Paul E.,Ren, Minghuan,Suto, Mark,Bennett, Brydon L.,Manning, Anthony,Ransone, Lynn,Spooner, Cheryl,Desai, Sonal,Ow, Arnie,Totsuka, Ryuichi,Tsao, Peter,Toriumi, Wataru
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p. 4077 - 4080
(2007/10/03)
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- Quinazoline analogs and related compounds and methods for treating inflammatory conditions
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Compounds having utility as anti-inflammatory agents in general and, more specifically, for the prevention and/or treatment of immunoinflammatory and autoimmune diseases are disclosed. The compounds are quinazoline-containing compounds. Methods are also d
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- Aziridination of alkenes using 3-acetoxyamino-2-trifluoromethylquinazolin-4(3H)-one
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Oxidation of 3-amino-2-trifluoromethylquinazolin-4(3H)-one 6 with lead tetraacetate in dichloromethane gives the title 3-acetoxyamino derivative 7 which is isolable at room temperature and considerably more stable than the corresponding 2-alkyl substituted analogues. Compound 7 aziridinates alkenes in yields which are consistently higher than those from the 2-alkyl substituted analogues. Aziridinations using 3-acetoxyaminoquinazolinones bearing other electron-withdrawing groups on the 2-position of the quinazolinone ring have been examined.
- Atkinson, Robert S.,Coogan, Michael P.,Cornell, Clive L.
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p. 157 - 166
(2007/10/03)
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- 1-aryl-3-(3,4-dihydro-4-oxo-3-quinazolinyl)urea fungicidal agents
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1-Aryl-3-(3,4-dihydro-4-oxo-3-quinazolinyl)-urea compounds which are effective for the control of prevention of phytopathogenic fungi are described. A method for the fungicidal use of said compounds, fungicidal compositions containing said compounds and m
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- 1-aryl-3-(3.4-dihydro-4-oxo-3-quinazolinyl)urea fungicidal agents
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1-Aryl-3-(3,4-dihydro-4-oxo-3-quinazolinyl)urea compounds which are effective for the control or prevention of phytopathogenic fungi are described. A method for the fungicidal use of said compounds and fungicidal compositions containing said compounds is
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- Studies of Rutaecarpine and Related Quinazolinocarboline Alkaloids
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Quinazolinocarboline alkaloids, e.g., rutaecarpine (1), can readily be synthesized by treating tryptamine with 2-(trifluoromethyl)-4H-3,1-benzoxazin-4-one (quickly generated in situ from trifluoroacetic anhydride (TFAA) and 2H-3,1-benzoxazine-2,4(1H)-dione.The product formed, 3--2-(trifluoromethyl)-4-(3H)-quinazolinone (5), is then cyclized (HCl/HOAc) to 13b-(trifluoromethyl)-13b,14-dihydrorutaecarpine (6), whereupon CF3H is eliminated by treatment with base.The sequence can conveniently be performed as a three-reaction one-pot procedure giving rutaecarpine (1) in 99percent yield within 3h.The approach can readily be extended to the synthesis of evodiamine (2), 13,13b-dehydroevodiamine (38a), and 13b,14-dihydrorutaecarpine (21).Thus treatment of 3--4(3H)-quinazolinone (19) with TFAA affected cyclization to 13b-(trifluoroacetyl)-13b,14-dihydrorutaecarpine (20), which can be readily hydrolyzed to 13b,14-dihydrorutaecarpine (21).
- Bergman, Jan,Bergman, Solveig
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p. 1246 - 1255
(2007/10/02)
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- New Route to N-Aryl and N-Heteroaryl Derivatives of 4-Hydroxy-3-quinolinecarboxamides
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The synthesis of N-aryl and N-heteroaryl substituted 4-hydroxy-3-quinolinecarboxamides 1 is described.The attack of dianions 12 of N-aryl substituted acetamides on the C-4 carbonyl of 4H-3,1-benzoxazin-4-ones 11 gave rise to ketoamides 13, which smoothly cyclized in the presence of bases to afford quinolinecarboxamides 1.By this method, a large number of 2-substituted 4-hydroxyquinolinecarboxamides can be prepared.
- Clemence, Francois,Martret, Odile Le,Collard, Jeannine
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p. 1345 - 1353
(2007/10/02)
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- SYNTHESIS OF RUTECARPINE AND RELATED INDOLE ALKALOIDS
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A new route to quinazolinocarboline alkaloids, involving elimination of CF3- in the final step has been developed.
- Bergman, Jan,Bergman, Solveig
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p. 347 - 350
(2007/10/02)
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- Rigid analogs of indomethacin
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10 Chloro 2 methoxy 5 methyl 7 H pyrrolo [3,2,1 de]phenanthrid 7 one 4 acetic acid and its deschloro analog were synthesized as rigid analogs of indomethacin. The chloro analog was found to be inactive in a standard in vivo guinea pig uv erythema assay.
- Olson,Wheeler,Wells
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p. 167 - 171
(2007/10/08)
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