- 2-bromo-2-nitropropane/zn promoted reductive cyclizations of ortho-carbonyl, imino, or azo substituted nitrobenzenes
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Under the mild conditions, reductive cyclizations of 2-nitrobenzaldehydes, 2'-nitroacetophenone, and N-(2-nitrobenzylidene)anilines were accomplished in the presence of 2-bromo-2-nitropropane/Zn in methanolic solution. Under the similar conditions in MeOH/CH2Cl2, o-nitro-substituted phenylazobenzenes have been converted into 2-aryl-2H-benzotriazoles via reductive cyclizations that are widely used as UV absorbers. Synthesis and mechanistic details are discussed.
- Kim, Byeong Hyo,Lee, Yoon Seok,Kwon, Woong,Jin, Youngoo,Tak, Jung Ae,Jun, Young Moo,Baik, Woonphil,Lee, Byung Min
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- 2-Bromo-2-nitropropane/Zn promoted reductive cyclizations of ortho-substituted nitroarenes toward 2,1-benzisoxazole derivatives
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Under the mild conditions, reductive cyclizations of 2-nitrobenzaldehydes or 2′-nitroacetophenone towards 2,1-benzisoxazoles were accomplished in the presence of 2-bromo-2-nitropropane/Zn in methanolic solution. The synthetic utility and the role of 2-bromo-2-nitropropane were investigated.
- Kim, Byeong Hyo,Jun, Young Moo,Kim, Tae Kyu,Lee, Yoon Seok,Baik, Woonphil,Lee, Byung Min
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- Electrochemical synthesis of 2,1-benzisoxazoles by controlled potential cathodic electrolysis
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Using a divided cell, reductive cyclization of nitroarene compounds into 2,1-benzisoxazoles in .mild conditions was successfully accomplished by the controlled potential cathodic electrolysis reactions. Optimum reaction potential of each reaction was determined based on cyclic voltametric behavior in methanol solution at Pb or Ft cathode, and Pt anode.
- Kim, Byeong Hyo,Jim, Young Moo,Choi, Yong Rack,Lee, Doo Byung,Baik, Woonphil
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- Rh(iii)-Catalyzed tandem indole C4-arylamination/annulation with anthranils: Access to indoloquinolines and their application in photophysical studies
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An efficient Rh(iii)-catalyzed straightforward strategy was developed for the tandem C4 arylamination/annulation of indole derivatives with anthranil to provide indoloquinoline moieties. This method is simple and regioselective with a wide scope and functional group tolerance. Mechanistic studies revealed the important role of the newly installed azacycle in the conversion of O-protected aldoximes to their cyano derivatives. Studies were carried out to explore the promising photophysical properties of the obtained indoloquinoline derivatives.
- Biswas, Aniruddha,Bera, Satabdi,Poddar, Puja,Dhara, Dibakar,Samanta, Rajarshi
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supporting information
p. 1440 - 1443
(2020/02/11)
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- Gold-Catalyzed Intermolecular Formal [4 + 2 + 2]-Cycloaddition of Anthranils with Allenamides
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The construction of eight-membered rings is a challenging issue due to unfavorable transannular strain and entropic barriers. We report herein a gold-catalyzed formal [4 + 2 + 2] cycloaddition reaction of anthranils with allenamides to deliver oxa-bridged eight-membered heterocycles in accepted yields with unique E/Z configuration. Moreover, the asymmetric [4 + 2 + 2] cycloaddition by using chiral phosphoramidite gold catalyst has also been conducted.
- Wang, Cheng,Xu, Guangyang,Shao, Ying,Tang, Shengbiao,Sun, Jiangtao
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supporting information
p. 5990 - 5994
(2020/08/12)
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- Pd-Catalyzed Dearomatization of Anthranils with Vinylcyclopropanes by [4+3] Cyclization Reaction
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Dearomatization of anthranils with vinylcyclopropanes (VCPs) by Pd-catalyzed [4+3] cyclization reaction has been realized. In the presence of a catalytic amount of borane as an activator, bridged cyclic products were obtained in good to excellent yields with excellent stereoselectivities. By introducing a chiral PHOX ligand (L5), asymmetric dearomatization reactions of anthranils with vinylcyclopropanes proceeded with excellent enantioselectivity. Borane plays a key role for the reactivity, likely owing to the formation of a borane–anthranil complex which has been confirmed by NMR experiments.
- Cheng, Qiang,Xie, Jia-Hao,Weng, Yue-Cheng,You, Shu-Li
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supporting information
p. 5739 - 5743
(2019/03/26)
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- Vasicine from Adhatoda vasica as an organocatalyst for metal-free Henry reaction and reductive heterocyclization of o-nitroacylbenzenes
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Vasicine, a quinazoline alkaloid, from the leaves of Adhatoda vasica, has been utilized as an efficient catalyst for metal and base free Henry reaction of various aldehydes with nitro alkanes. The method can be used in the synthesis of various β-nitro alcohols under mild reaction conditions without use of hazardous organic solvents and expensive catalysts. Vasicine is also applied successfully for one pot synthesis of 2,1-benzisoxazoles from o-nitroacylbenzenes in good yields under mild conditions.
- Sharma, Sushila,Kumar, Manoranjan,Bhatt, Vinod,Nayal, Onkar S.,Thakur, Maheshwar S.,Kumar, Neeraj,Singh, Bikram,Sharma, Upendra
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supporting information
p. 5003 - 5008
(2016/10/25)
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- Unusual reactivity of aryl aldehydes with triethyl phosphite and zinc bromide: A facile preparation of epoxides, benzisoxazoles, and α-hydroxy phosphonate esters
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Abstract A facile preparation of trans-epoxides was achieved by a (EtO)3P-ZnBr2-mediated deoxygenation reaction of the corresponding 2-nitrobenzaldehydes. The sterically hindered analogues of 2-nitrobenzaldehyde underwent a reaction
- Raju, Potharaju,Gobi Rajeshwaran, Ganesan,Nandakumar, Meganathan,Mohanakrishnan, Arasambattu K.
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p. 3513 - 3523
(2015/06/08)
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- Reductive heterocyclizations via indium-iodine-promoted conversion of 2-nitroaryl imines or 2-nitroarenes to 2,3-diaryl-substituted indazoles
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While N-(2-nitrobenzylidene)anilines produced mixtures of 2,1-benzisoxazoles and 3-anilino-2-aryl-2H-indazoles in the presence of indium and iodine in MeOH, N-(2-nitrobenzylidene)anilines were transformed into 3-anilino-2-aryl-2H-indazoles as the predominant major product through the change of the solvent from protic MeOH to aprotic THF. In an indium-mediated one-pot reductive reaction, 2-benzaldehydes and anilines in THF were also successfully transformed into the corresponding indazoles. This journal is The Royal Society of Chemistry.
- Ahn, Gil Hwan,Lee, Jung June,Jun, Young Moo,Lee, Byung Min,Kim, Byeong Hyo
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p. 2472 - 2485
(2008/02/13)
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- Reductive heterocyclizations via indium/iodine-promoted one-pot conversion of 2-nitroaryl aldehydes, ketones, and imines
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2-Nitroaryl aldehydes, ketones, and imines were reductively cyclized to 2,1-benzisoxazoles with good yields in the presence of indium and iodine in MeOH. Under a similar condition, N-(2-nitrobenzylidene)anilines were produced mixtures of 2,1-benzisoxazoles and 3-anilino-2-phenyl-2H-indazoles.
- Han, Rongbi,Son, Kee In,Ahn, Gil Hwan,Jun, Young Moo,Lee, Byung Min,Park, Younbong,Kim, Byeong Hyo
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p. 7295 - 7299
(2007/10/03)
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- Indium mediated reductive heterocyclization of 2-nitroacylbenzenes or 2- nitroiminobenzenes toward 2,1-benzisoxazoles in aqueous media
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2-Nitro-substituted acylbenzenes or iminobenzenes such as 2- nitrobenzaldehydes, 2'-nitroacetophenone, and N(2-nitrobenzylidene)anilines were cyclized toward 2,1-benzisoxazoles in the presence of 2-bromo-2- nitropropane and indium in an MeOH/H2O solution in excellent yields. (C) 2000 Elsevier Science Ltd.
- Kim, Byeong Hyo,Jin, Youngoo,Jun, Young Moo,Han, Rongbi,Baik, Woonphil,Lee, Byung Min
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p. 2137 - 2140
(2007/10/03)
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- Reductive reactions of nitroarenes in the presence of allyl bromide and zinc dust
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Under the mild condition, allyl bromide/Zn mediated reductive N,O- diallylation of nitrobenzene was observed. In case of o-nitroarenes such as 2-nitrobenzaldehyde derivatives, 2'-nitroacetophenone, and N-(2- nitrobenzylidene)anilines, reductive cyclizations were accomplished in good to excellent yields. Synthesis and mechanistic details are discussed.
- Kim, Byeong Hyo,Kim, Tae Kyu,Cheong, Jae Wook,Lee, Sang Woo,Jun, Young Moo,Baik, Woonphil,Lee, Byung Min
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p. 1921 - 1928
(2007/10/03)
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