4765-51-9Relevant academic research and scientific papers
Recyclable Heterogeneous Palladium-Catalyzed Cyclocarbonylation of 2-Iodoanilines with Acyl Chlorides in the Biomass-Derived Solvent 2-Methyltetrahydrofuran
Hao, Wenyan,Xu, Zhaotao,Zhou, Zebiao,Cai, Mingzhong
, p. 8522 - 8532 (2020/07/16)
A highly efficient, green palladium-catalyzed cyclocarbonylation of 2-iodoanilines with acyl chlorides has been developed that proceeds smoothly in a biomass-derived solvent 2-methyltetrahydrofuran with N,N-diisopropylethylamine as base at 100 °C under 20 bar of carbon monoxide using an 2-aminoethylamino-modified MCM-41-anchored palladium acetate complex [2N-MCM-41-Pd(OAc)2] as a heterogeneous catalyst, yielding a wide variety of 2-substituted 4H-3,1-benzoxazin-4-one derivatives in good to excellent yields. This supported palladium catalyst could be facilely obtained by a two-step procedure from easily available starting materials and readily recovered via a simple filtration process and recycled at least 8 times without any apparent decrease in catalytic efficiency. The developed methodology not only avoids the use of toxic solvents such as tetrahydrofuran and dimethylformamide but also solves the basic problem of expensive palladium catalyst recovery and reuse and prevents effectively palladium contamination of the desired product.
Domino synthesis of pyrimido and imidazoquinazolinones
Fathalla, Walid,Nofal, Eman Y.,El-Moneim, Mohamed Abd
, p. 1266 - 1274 (2020/01/21)
A simple method for the synthesis of N-alkyl-2-arylquinazolin-4-amines, methyl 4-((2-arylquinazolin-4-yl)amino) butanoates, 6-aryl-2,3-dihydro-4H-pyrimido[1,2-c]quinazolin-4-ones, and 5-arylimidazo[1,2-c]quinazolin-3(2H)-ones has been described. It involves a simple reaction of N-(2-cyanophenyl)-substitutedbenzimidoyl chlorides with alkylamine, γ-aminobutyric acid, β-alanine, l-alanine, and glycine methyl esters hydrochloride in acetonitrile to afford the desired compounds after a series of instantaneous reactions that include Dimroth rearrangement. The reaction involves reflux for 12 hours, simple addition of reagents to an in situ generated benzimidoyl chloride, and simple workup, to form 21 examples of pure compounds in high yields. The active intermediate N-(2-cyanophenyl)-substitutedbenzimidoyl chlorides were formed by the reaction of N-(2-cyanophenyl)-substitutedbenzamides with thionyl chloride in a one-pot strategy. The alternative method described for this preparation deals with an exhausting multistep reactions starting from anthranilic acid.
Palladium (0)-catalyzed C(sp2)-H oxygenation with carboxylic acids
Gong, Ai-Jun,Li, Xu-Qin,Vu, Huu-Manh,Yong, Jia-Yuan
supporting information, (2020/02/15)
Palladium (0)-catalyzed Ortho-benzoxylation of the sp2 C–H bond of arylbenzoxazinones with carboxylic acid is reported. With benzoxazinone as directing group, the reaction went smoothly under the benign condition and gave the desired product wi
Oxidative NHC catalysis for base-free synthesis of benzoxazinones and benzoazoles by thermal activated NHCs precursor ionic liquid catalyst using air as oxidant
Guan, Jiali,Liu, Wei,Liu, Yuchen,Song, Zhibin,Tao, Duan-Jian,Yan, Jieying,Yuan, Jian-Jun,Zhou, Youkang
, (2020/05/25)
A reusable thermal activated NHC precursor ionic liquid catalyst ([BMIm]2[WO4]) has been prepared and developed for the synthesis of nitrogen-containing heterocycles such as benzoxazinones and benzoazoles through imines activation. [BMIm]2[WO4] exhibited the good activity for the base-free condensation and oxidative NHC catalysis tandem under air atmosphere. The catalyst can be recovered and reused for at least five runs in gram scale synthesis without any decrease in catalytic activity. Furthermore, the control experiments demonstrated that the reaction involved formation of aromatic aldimines, NHC-catalyzed oxidative formation of imidoyl azoliums and intramolecular cyclization to generate the product.
Silver-Mediated Synthesis of 4H-Benzoxazin-4-ones by Intramolecular Decarboxylative O-Acylation Reactions with α-Oxocarboxylic Acid
Bharathimohan, Kuppusamy,Ponpandian, Thanasekaran,Jafar, Ahamed A.
, p. 2806 - 2813 (2017/05/29)
The first example of an intramolecular decarboxylative acylation reaction for the synthesis of 4H-benzoxazin-4-one derivatives has been described. The silver-mediated reaction has a broad substrate scope and provides a mild and rapid approach to the corre
Direct oxidative cascade cyclisation of 2-aminobenzoic acid and arylaldehydes to aryl 4H-3,1-benzoxazin-4-ones with oxone
Munusamy, Sathishkumar,Muralidharan, Vivek Panyam,Iyer, Sathiyanarayanan Kulathu
supporting information, p. 520 - 523 (2017/01/16)
This paper presents a methodology of oxidative cascade cyclisation of 2-aminobenzoic acids and arylaldehyde using I2as a catalyst and an environmentally benign oxidant oxone. This method displays facile access to a diverse range of substituted aryl 4H-3,1-benzoxazin-4-ones. This synthetic methodology has many advantages such as: (1) easy availability of starting material, (2) transition metal-free condition (3) use of an environmentally benign oxidant.
BCL-3 INHIBITORS
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Paragraph 000366; 000367; 000368; 000369; 000370, (2016/04/06)
The present application relates to compounds of any one of Formulae I, Ia, Ib, Ic, Id, Ie, and If. Compounds of Formula (I) have the structure, wherein A, B, Y, Z, R2, R4, R5, R6, Rq and q are as defined herein. The compounds can be used as inhibitors of Bcl-3 and can be used for the treatment of cancer, particularly metastatic cancer.
RETRACTED ARTICLE: Palladium-Catalyzed Decarboxylative Selective Acylation of 4H-Benzo[d][1,3]oxazin-4-one Derivatives with α-Oxo Carboxylic acids via Preferential Cyclic Imine-N-Directed Aryl C-H Activation
Majhi, Biju,Kundu, Debasish,Ghosh, Tubai,Ranu, Brindaban C.
, p. 283 - 295 (2016/02/16)
The benzoxazine scaffolds are of much interest as they are found in a large array of natural products and pharmaceutical drugs with diverse activities. We have developed a palladium-catalyzed decarboxylative selective mono- and bis-acylation of 4H-benzo[d
Ruthenium(II) Catalyzed Regiospecific C-H/O-H Annulations of Directing Arenes via Weak Coordination
Banerjee, Arghya,Santra, Sourav Kumar,Mohanta, Prakash Ranjan,Patel, Bhisma K.
supporting information, p. 5678 - 5681 (2015/12/01)
Ruthenium(II) catalyzed oxidative C-H/O-H annulations have been demonstrated using two different directing arenes viz. 2-arylquinolinone and 2-arylbenzoxazinone with internal alkynes. Regiospecific annulations have been observed for both directing arenes via the assistance of weaker carbonyl oxygen in the presence of a stronger nitrogen-directing site. In this substrate-controlled convergent protocol the weaker directing group dictates the annulation path.
Carbonylative synthesis of phthalimides and benzoxazinones by using phenyl formate as a carbon monoxide source
Chavan, Sujit P.,Bhanage, Bhalchandra M.
, p. 2405 - 2410 (2015/04/22)
A simple and efficient palladium-catalyzed carbonylative cyclization of N-substituted 2-iodobenzamides and 2-iodoanilides was investigated for the synthesis of phthalimides and benzoxazinones, respectively, by using phenyl formate as a CO source. The present catalytic protocol circumvents the use of an expensive phosphine ligand as well as solvent in the case of the phthalimide synthesis. Moreover, mild reaction conditions and a tolerance of various functional groups enhance the general applicability of this method.
