- Recent developments in the chemistry of heteroaromatic N -oxides
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Selected developments in the chemistry of heteroaromatic N-oxides since 2001 are presented in this review. The use of these N-oxides, both in late-transition-metal-catalyzed oxidations of carbon-carbon triple bonds and in regioselective C-H functionalizations of the heteroarene, are contemporary topics of interest and the focus of the discussion. 1 Introduction 2 Synthesis of Heteroaromatic N-Oxides 2.1 Direct Oxidation of Hindered Heteroarenes 2.2 Through Construction of Heteroaromatic Rings 3 Heteroaromatic N-Oxides as Oxidants 3.1 Alkyne Oxidation 3.2 Allene Oxidation 3.3 Carbene Oxidation 4 Heteroaromatic N-Oxides as Substrates 4.1 Deoxygenative ortho-C-H Functionalization with Prior Activation 4.2 Deoxygenative ortho-C-H Functionalization with Nonstabilized Carbanions 4.3 Nondeoxygenative C-H Functionalization 4.3.1 ortho-C-H Functionalization 4.3.2 N-Oxide Directed ortho-Alkyl C-H Functionalization 4.3.3 N-Oxide Directed Remote C-H Functionalization 4.4 1,3-Dipolar Cycloaddition 5 Conclusion and Outlook.
- Wang, Youliang,Zhang, Liming
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- Acid-induced conformational alteration of cis-preferential aromatic amides bearing N-methyl-N-(2-pyridyl) moiety
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A series of cis-preferential aromatic N-methyl amides was designed and synthesized, and acid-induced conformational alteration of these compounds was investigated by means of NMR measurements in solution and X-ray crystal structure analysis. Compounds with a terminal N-methyl-N-(2-pyridyl) amide unit showed acid-induced conformational change from cis to trans, while those with a terminal N-methyl-2-pyridinecarboxamide unit showed a change of the carbonyl orientation from anti to syn with retention of cis conformation.
- Okamoto, Iwao,Terashima, Masayuki,Masu, Hyuma,Nabeta, Mayumi,Ono, Kaori,Morita, Nobuyoshi,Katagiri, Kosuke,Azumaya, Isao,Tamura, Osamu
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experimental part
p. 8536 - 8543
(2011/11/28)
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- A mild method for the formation and in situ reaction of imidoyl chlorides: conversion of pyridine-1-oxides to 2-aminopyridine amides.
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[reaction: see text] A mild, practical, one-pot method for the generation of imidoyl chlorides and their subsequent in situ reaction with pyridine-1-oxides is described. The imidoyl chlorides were formed from the reaction of secondary amides with a stoich
- Manley, Peter J,Bilodeau, Mark T
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p. 3127 - 3129
(2007/10/03)
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- Convenient Syntheses of Alkyl β-Resorcylate Derivatives
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Syntheses of methyl 2,4-dihydroxy-6-methyl- (1a) and -3,6-dimethylbenzoates (1b) and methyl 2,4-dihydroxy-6-pentylbenzoate (1c) are described.Condensation reactions of dimethyl sodiomalonate with the dianion derived from pentane-2,4-dione or the dimerisation of the methyl acetoacetate dianion or the acetylation of the trianion derived from methyl 3,5,7-trioxo-octanoate gave (1a) (78percent) after work-up at pH 9.Analogous convenient, short, optimised syntheses of (1b and c) are given in detail.
- Barrett, Anthony G. M.,Morris, Timothy M.,Barton, Derek H. R.
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p. 2272 - 2277
(2007/10/02)
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