- 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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- 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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- 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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p. 2581 - 2592
(2007/10/03)
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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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p. 235 - 240
(2007/10/03)
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- Thermal Stability Studies on a Homologous Series of Nitroarenes
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The thermal stabilities of a number of nitroarenes were examined in solution and in condensed phase.In general, increasing the number of nitro groups decreased thermal stability.Changing the substituent on 1-X-2,4,6-trinitrobenzene from X = H to NH2 to CH3 to OH accelerated decomposition; this effect was attributed to increased ease of intramolecular proton transfer to an ortho nitro group, thus weakening the carbon-nitrogen bond.In solution, the effect of increasing substitution from n = 1 to n = 3 on Xn(NO2)3C6H3-n was uniformly that of decreasing the thermal stability of the species.However, in condensed phase, results suggested that crystal habit may be more important than molecular structure; for X = Br, CH3, and NH2, the more substituted species was the more stable.
- Oxley, Jimmie C.,Smith, James L.,Ye, Hong,McKenney, Robert L.,Bolduc, Paul R.
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p. 9593 - 9602
(2007/10/02)
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