- Direct synthesis of benzoxazinones via Cp*Co(III)-catalyzed C–H activation and annulation of sulfoxonium ylides with dioxazolones
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A highly novel and direct synthesis of benzoxazinones was developed via Cp*Co(III)-catalyzed C–H activation and [3 + 3] annulation between sulfoxonium ylides and dioxazolones. The reaction is conducted under base-free conditions and tolerates various functional groups. Starting from diverse readily available sulfoxonium ylides and dioxazolones, a variety of benzoxazinones could be synthesized in one step in 32%-75% yields.
- Yu, Yongqi,Xia, Zhen,Wu, Qianlong,Liu, Da,Yu, Lin,Xiao, Yuanjiu,Tan, Ze,Deng, Wei,Zhu, Gangguo
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p. 1263 - 1266
(2020/10/08)
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- One pot synthesis of some new N-allyl and N-benzyl quinazolinones and their anti-inflammatory activity
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The simple and more reliable one-pot synthesis of some novel compounds of allyl/Benzyl quinazolinone (4aa-4bd) with good yields from readily available derivatives of anthranilic acid and benzoyl chloride was also reported. Interestingly, as compared to Di
- Sudula, Sudharshan Reddy,Jala, Ranjith,Siddoju, Kavitha,Ega, Jagadeesh Kumar
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- From Methaqualone and Beyond: Structure - Activity Relationship of 6-, 7-, and 8-Substituted 2,3-Diphenyl-quinazolin-4(3H)-ones and in Silico Prediction of Putative Binding Modes of Quinazolin-4(3H)-ones as Positive Allosteric Modulators of GABAA
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Methaqualone (2-methyl-3-(o-tolyl)-quinazolin-4(3H)-one, MTQ) is a moderately potent positive allosteric modulator (PAM) of GABAA receptors (GABAARs). In a previous structure-activity relationship (SAR) study probing the importance of 2- and 3-substituent
- Wang, Peng-Fei,Jensen, Anders A.,Bunch, Lennart
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p. 4362 - 4375
(2020/11/30)
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- Recyclable Heterogeneous Palladium-Catalyzed Carbonylative Cyclization of 2-Iodoanilines with Aryl Iodides Leading to 2-Arylbenzoxazinones
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A highly efficient and practical heterogeneous palladium-catalyzed carbonylative coupling of 2-iodoanilines with aryl iodides has been developed. The reaction occurs smoothly in toluene at 110 °C with N, N -diisopropylethylamine as base under carbon monoxide (5 bar) and offers a general and powerful tool for the construction of various valuable 2-arylbenzoxazinones with excellent atom-economy, high functional group tolerance, good to high yields, and easy recyclability of the palladium catalyst. The reaction is the first example of heterogeneous palladium-catalyzed carbonylative coupling for the preparation of diverse 2-arylbenzoxazinones from commercially easily available 2-iodoanilines and aryl iodides.
- Cai, Mingzhong,Huang, Bin,Xu, Zhaotao,Zhou, Zebiao
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p. 581 - 590
(2020/02/13)
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- Palladium (0)-catalyzed C(sp2)-H oxygenation with carboxylic acids
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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
- Gong, Ai-Jun,Li, Xu-Qin,Vu, Huu-Manh,Yong, Jia-Yuan
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supporting information
(2020/02/15)
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- Benzoxazinone compound of the horticultural fungicide (by machine translation)
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[Problem] in the production of agricultural and horticultural crops, new horticultural fungicide containing the same. The present invention is [solution] horticultural fungicide containing, equation (1) (1)[In the formula, The R, a hydrogen atom, a haloge
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Paragraph 0077
(2019/04/13)
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- One-Pot Synthesis of 2-Arylbenzoxazinones from 2-Arylindoles with (Diacetoxyiodo)benzene as the Sole Oxidant
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A series of synthetically interesting 2-arylbenzoxazinones was prepared from 2-arylindoles by an efficient oxidative reaction mediated by (diacetoxyiodo)benzene [PhI(OAc) 2 ] and assisted by water. PhI(OAc) 2 was used as the sole oxi
- Shang, Xian-Xing,Vu, Huu-Manh,Li, Xu-Qin
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supporting information
p. 377 - 383
(2017/10/30)
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- Design, synthesis and pharmacological evaluation of 2-phenyl quinazolin-4-one derivatives as anticolorectal cancer and anti-inflammatory agent
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Quinazoline derivatives are heterocyclic compounds that acts as important structural lead for the discovery of effective therapeutic agents. The anti-inflammatory activity along with cytotoxicity helps to reduce the inflammation and pain associated with carcinoma. Derivatives of quinazoline-4-one were preliminary screened and in silico molecular modelling studies using Autodock were performed. In the docking study, ligands were docked against anticancer and anti-inflammatory targets. In silico analysis revealed that the compounds with aromatic substitution at 3rd and halogen substitution at 6th or 7th positions possess lesser side effects and have more potent antitumor activity. Based upon these results 12 compounds were selected, synthesized, characterized and screened for their in vitro, anti-inflammatory, antioxidant and anticancer activities. From the in vitro studies, compounds QA4, QA7 and QB1 showed good anticancer, anti-inflammatory and antioxidant activity when compared to the standard.
- Bosco, Deena,Balakrishnan, Ashitha,Mishra, Rohan,Aneesh
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p. 2677 - 2685
(2018/11/20)
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- Mechanochemical Synthesis of Substituted 4H-3,1-Benzoxazin-4-ones, 2-Aminobenzoxazin-4-ones, and 2-Amino-4H-3,1-benzothiazin-4-ones Mediated by 2,4,6-Trichloro-1,3,5-triazine and Triphenylphosphine
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A mild and convenient approach for the synthesis of 2-substituted 4H-3,1-benzoxazin-4-ones, 2-aminobenzoxazin-4-ones, and 2-amino-4H-3,1-benzothiazin-4-ones under solvent-assisted grinding is reported. In the presence of 2,4,6-trichloro-1,3,5-triazine and
- Pattarawarapan, Mookda,Wet-Osot, Sirawit,Yamano, Dolnapa,Phakhodee, Wong
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p. 589 - 592
(2017/03/11)
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- Copper-Catalyzed C–N, C–O Coupling Reaction of Arylglyoxylic Acids with Isatins
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The copper(II)-catalyzed decarboxylative coupling reactions of arylglyoxylic acids with isatins afford 4H-benzo[d][1,3]oxazin-4-ones via decarbonylation and concurrent C–N, C–O bond formation. (Figure presented.).
- Prakash, Rashmi,Gogoi, Sanjib
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supporting information
p. 3046 - 3049
(2016/10/09)
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- TBHP/CoCl2-mediated intramolecular oxidative cyclization of N-(2-formylphenyl)amides: An approach to the construction of 4H-3,1-benzoxazin-4-ones
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The intramolecular oxidative cyclization of N-(2-formylphenyl)amides has been realized through an oxidative C(sp2)-O(sp2) bond-forming reaction between an aldehyde carbon and amide oxygen. This new strategy, which uses tert-butyl hydroperoxide (TBHP) as an oxidant and CoCl2 as the catalyst, allows for the efficient Co-catalyzed synthesis of useful benzoxazin-4-one derivatives and features readily available starting materials and mild reaction conditions. The intramolecular cyclization of N-(2-formylphenyl)amides has been realized through an oxidative C(sp2)-O(sp2) bond-forming reaction between an aldehyde carbon and amide oxygen. This new strategy, which uses tert-butyl hydroperoxide (TBHP) as the oxidant and CoCl2 as the catalyst, allows for the efficient Co-catalyzed synthesis of useful benzoxazin-4-one derivatives.
- Yu, Junchao,Zhang-Negrerie, Daisy,Du, Yunfei
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p. 562 - 568
(2016/02/18)
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- Concise synthesis of cyclic carbonyl compounds from haloarenes using phenyl formate as the carbonyl source
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Various cyclic carbonyl compounds were concisely synthesized by carbonylative cyclization of haloarenes bearing nucleophilic moieties under Pd catalysis. A broad substrate scope and a feasible large-scale synthesis clearly demonstrate the high applicability of the reaction as a general, user-friendly method for access to cyclic carbonyl compounds.
- Konishi, Hideyuki,Nagase, Hiroki,Manabe, Kei
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supporting information
p. 1854 - 1857
(2015/01/30)
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- Carbonylative synthesis of phthalimides and benzoxazinones by using phenyl formate as a carbon monoxide source
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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.
- Chavan, Sujit P.,Bhanage, Bhalchandra M.
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p. 2405 - 2410
(2015/04/22)
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- Nucleophilic ring-opening of benzoxazinones by DBU: Some observations
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This communication demonstrates the formation of an unusual nucleophilic ring opening of benzoxazinones by 1,8-diazabicycloundec-7-ene (DBU). This observation contradicts the intrinsic feature of a hindered nonnucleophilic base like DBU. Confirmation of t
- Baravkar, Sachin B.,Roy, Arup,Gawade, Rupesh L.,Puranik, Vedavati G.,Sanjayan, Gangadhar J.
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p. 2955 - 2960
(2014/11/07)
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- One-pot approach to 2-arylbenzoxazinone derivatives from 2-alkynylanilines using copper-mediated tandem reactions
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In this study, we describe a one-pot method to obtain a variety of 2-arylbenzoxazinones and N-benzoyl anthranilic acid by using a copper catalyst and molecular oxygen as oxidants. This protocol involves tandem cyclization and oxidative processes of 2-alkynylanilines to afford significant motifs in synthetic and medicinal chemistry with moderate yields. We also demonstrated that combining the Sonogashira coupling and the developed method realized the synthesis of 2-arylbenzoxazinones derivatives from commercially available 2-iodoanilines and terminal acetylenes.
- Yamashita, Mitsuaki,Iida, Akira
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p. 5746 - 5751
(2015/03/30)
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- [bmIm]OH: An efficient basic catalyst for the synthesis of 4H-benzo[d][1,3-]oxazin-4-one derivatives in solvent-free conditions
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Reusable [bmIm]OH was found to be a highly efficient renewable homogenous catalyst for the rapid and convenient synthesis of benzoxazine-4-one derivatives from o-iodobenzoic-acid and benzonitrile at 75 °C in moderate to good yields. This methodology provides a facile and straightforward path to construct other related heterocycles in an eco-compatible fashion.
- Waseem, Malik Abdul,Shireen,Srivastava, Anjali,Srivastava, Arjita,Rahila,Siddiqui
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supporting information
p. 6072 - 6076
(2015/01/08)
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- Copper-mediated oxidative tandem reactions with molecular oxygen: Synthesis of 2-arylbenzoxazinone derivatives from indoles
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We developed an efficient method for the transformation of indoles by utilizing a copper catalyst and molecular oxygen as the oxidant. The transformation involves a tandem oxidative process of 2-arylindoles. Our reaction afforded a variety of N-benzoyl an
- Yamashita, Mitsuaki,Iida, Akira
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supporting information
p. 2991 - 2993
(2014/05/06)
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- Oxidation of 2-arylindoles for synthesis of 2-arylbenzoxazinones with oxone as the sole oxidant
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A novel and efficient method for the oxidation of 2-arylindoles to synthesize 2-arylbenzoxazinones utilizing oxone as the sole oxidant has been developed. The reaction tolerates a wide range of functional groups and allows quick and atom-economical assembly of a variety of valuable 2-arylbenzoxazinones in high yields.
- Lian, Xiao-Li,Lei, Hao,Quan, Xue-Jing,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
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p. 8196 - 8198
(2013/09/12)
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- Copper-catalyzed C-N bond formation/rearrangement sequence: Synthesis of 4H-3,1-benzoxazin-4-ones
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A facile and efficient copper-catalyzed method for the synthesis of 4H-3,1-benzoxazin-4-one derivatives has been developed. This procedure is based on a tandem intramolecular C-N coupling/rearrangement process. This method would provide a new and useful strategy for construction of N-heterocycles.
- Ge, Zhi-Yuan,Xu, Qiong-Ming,Fei, Xi'Ang-Dong,Tang, Ting,Zhu, Yong-Ming,Ji, Shun-Jun
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p. 4524 - 4529
(2013/06/05)
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- A convenient and general palladium-catalyzed carbonylative coupling for the synthesis of 2-arylbenzoxazinones
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CO and CO again: A new double carbonylation methodology for the synthesis of 2-arylbenzoxazinones has been developed (see scheme). Copyright
- Wu, Xiao-Feng,Schranck, Johannes,Neumann, Helfried,Beller, Matthias
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supporting information; experimental part
p. 12246 - 12249
(2011/12/02)
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- Synthesis and biological evaluation of new indazole derivatives
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New N-methyl and N-ethyl substitutions in the indazole nucleus are reported by reacting 3-(2-aminobenzamido)indazole and the appropriate trimethyl/triethyl orthobenzoate. Single crystal X-ray analysis confirms the N-ethylation position for the 3-(1-ethyl-1H-indazol-3-yl)-2-phenylquinazolin-4(3H)-one derivative 3f. Compounds 11a-d and 3a-d were tested to evaluate their antimicrobial, antiproliferative and COX inhibitory activities, showing scarce or moderately antiproliferative activity and some inhibitory activity against COX-1 and COX-2. ARKAT USA, Inc.
- Plescia, Salvatore,Raffa, Demetrio,Plescia, Fabiana,Casula, Giovanni,Maggio, Benedetta,Daidone, Giuseppe,Raimondi, Maria Valeria,Cusimano, Maria Grazia,Bombieri, Gabriella,Meneghetti, Fiorella
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experimental part
p. 163 - 177
(2010/12/25)
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- Compounds and methods for inhibiting mitotic progression
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This invention relates to compounds and methods for the treatment of cancer. In particular, the invention provides compounds that inhibit Aurora kinase, pharmaceutical compositions comprising the compounds, and methods of using the compounds for the treat
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Page/Page column 138
(2008/06/13)
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- Improved synthesis of 2-amino-5-chlorophenyl-2'-pyrrylketone, a key intermediate in the synthesis of HIV Tat-antagonists
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The reaction of a 2-phenylbenzoxazinone with pyrryl Grignard reagent is very efficient compared with that of a 2-methylbenzoxazinone. The title compound was prepared from 5-chloroanthranilic acid via the 2-phenylbenzoxazinone in 92% overall yield. This method was also successfully applied to the synthesis of 2-aminobenzophenones.
- Okabe,Sun
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p. 1861 - 1866
(2007/10/02)
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- Syntheses of 5-thienyl- and 5-furyl-substituted benzodiazepines: Probes of the pharmacophore for benzodiazepine receptor agonists
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The synthesis of 5-thienyl- and 5-furyl-substituted benzodiazepines is described. These compounds were employed to probe the lipophilic pocket (L3) of the benzodiazepine receptor (BzR) and to determine the effect of occupation of L3 on biological activity. Of the new analogs synthesized, the 5-(2-thienyl)-benzodiazepines 6a and 7a displayed high affinity for the BzR (IC50 28 and 18 nM, respectively) and exhibited both anticonvulsant (ED50 ~ 9 and 3 mg/kg) and muscle relaxant (ED50 ~ 10 and 7 mg/kg) activity. The 5-(3-thienyl)benzodiazepines 6d and 7d displayed only moderate affinity for the BzR (IC50 140 and 110 nM) and exhibited no biological activity (no anticonvulsant or muscle relaxant activity) at doses up to 40 mg/kg. The 5-(2-furyl)benzodiazepines (6b, 7b, 19b and 20b) exhibit low affinities for the BzR. These in vitro and in vivo findings are consistent with our model suggesting that pocket L3 is very sensitive to lipophilic effects. Thus, decreasing the lipophilicity of functional groups which occupy this region decreases ligand affinity at BzR. The 2'-halogen (F or Cl) substituent of the 5-phenylbenzodiazepines increases ligand affinity in vitro because the active conformation of the phenyl N(4)=C(5)-C(1')=C(2') moiety is syn rather than anti. The syn conformation permits the 2'-halogen (F or Cl) atom to interact at the hydrogen bonding site H2 and form a stable three-centered hydrogen bond in the proposed ligand binding cleft. The 3-thienyl and 2-furyl groups decrease the lipophilicity of the substituent which occupies L3 but do not form a hydrogen bond at H2, thus resulting in a diminished affinity at BzR.
- Zhang,Liu,Huang,Zhang,Koehler,Harris,Skolnick,Cook
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p. 483 - 496
(2007/10/02)
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- Production of 3-Benzoyl-2,1-benzisoxazoles, 2-Phenyl-4H-3,1-benzoxazin-4-ones, and Novel Quinolinone Derivatives from 2-Phenylquinolin-4(1H)-ones and Sodium Dichloroisocyanurate
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A simple synthesis of certain 3-benzoyl-2,1-benzisoxazoles 6 is accomplished via treatment of the corresponding 2-phenylquinolin-4(1H)-one 1 with sodium dichloroisocyanurate 2 in methanolic aq. alkali; the isomeric 2-phenyl-4H-3,1-benzoxazin-4-one 7 is al
- Staskun, Benjamin,Es, Theodorus van
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p. 511 - 516
(2007/10/02)
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- Reactions of 2-Isocyanatobenzoyl Chlorides with Phenylmagnesium Bromide: Synthesis of 2-Phenyl-3,1-benzoxazin-4(H)-ones, N-Benzoyl-2-aminobenzophenones, α-(2-Benzamidoaryl)benzohydrols and 6-Chloro-4,4-diphenyl-3,1-benzoxazin-2(4H)-one
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In the reaction of 2-isocyanatobenzoyl chloride (Ia) with phenylmagnesium bromide, the isocyanato group is found to be exclusively attacked by the Grignard reagent to give 2-phenyl-3,1-benzoxazin-4(H)-one (IIIa), N-benzoylanthranilic acid (IVa), N-benzoyl-2-aminobenzophenone (Va), and α-(2-benzamidophenyl)benzohydrol (VIa) depending on the mode of addition and the relative amounts of the Grignard reagent.However, in the case of 5-chloro-2-isocyanatobenzoyl chloride (Ib), the chloroformyl group is also found to react simultaneously, although to a smaller extent, to give 6-chloro-4,4-diphenyl-1,2-dihydro-3,1-benzoxazin-2(4H)-one (VIIb) in addition to 6-chloro-2-phenyl-3,1-benzoxazin-4(H)-one (IIIb), N-benzoyl-2-amino-5-chlorobenzophenone (Vb) and α-(2-benzamido-5-chlorophenyl)benzohydrol (VIb) depending on the reaction conditions.This is presumably due to the decreased reactivity of the isocyanato function due to the chloro group in the para-position.The reaction is believed to proceed through an acyclic intermediate complex which affords IIIa on work-up.PMR data of the compounds have also been discussed.
- Misra, B. K.,Rao, Y. R.,Mahapatra, S. N.
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p. 908 - 911
(2007/10/02)
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