Three‐Component Assembly and Divergent Ring‐Expansion Cascades of Functionalized 2‐Iminooxetanes

Yao, Weijun; Pan, Lianjie; Zhang, Yiping; Wang, Gang; Wang, Xiaoqin; Ma, Cheng

doi:10.1002/anie.201004685

Cited by 91 publications

(23 citation statements)

References 66 publications

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“…Their importance in synthetic and medicinal chemistry has attracted considerable attention for the development of new synthetic strategies for these compounds. [12][13][14][15] Azides have been widely used in organic reactions, [16][17][18] but recent progress on the direct transformation of simple hydrocarbons into N-containing compounds [18] through a nitrogenation strategy encouraged us to try the direct transformation of alkynes. Although metal-catalyzed C C bond cleavage involving alkyne metathesis has been disclosed, [9,10] direct CC bond cleavage to form nitriles (Scheme 1 h) is still unknown and remains both challenging and of great value.…”

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confidence: 99%

Silver‐Catalyzed Nitrogenation of Alkynes: A Direct Approach to Nitriles through CC Bond Cleavage

et al. 2013

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Silver‐Catalyzed Nitrogenation of Alkynes: A Direct Approach to Nitriles through CC Bond Cleavage

et al. 2013

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“…In particular, 1,5-disubstituted tetrazoles are very useful compounds in medicinal chemistry and important synthetic intermediates. [11,12] The application of azides for the direct synthesis of aryl nitriles [13] and alkenyl nitriles [13c-d] through C À H bond cleavage has been recently reported. These methods include: a) the reactions of ketones [3] or oximes [4] with sodium azide and hydrogen azides, b) the reactions of amides with sodium azides in the presence of phosphorus(V) chloride or triflic anhydride and [5] the reactions of amidrazones with dinitrogen tetroxide or nitrous acid, [6] c) the reactions of imidoyl chlorides [7a] or imidoylbenzotriazoles [7b] with sodium azides and, d) the reactions of nitriles with alkyl azides.…”

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Implanting Nitrogen into Hydrocarbon Molecules through CH and CC Bond Cleavages: A Direct Approach to Tetrazoles

et al. 2011

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The development of novel methods for the preparation of tetrazoles is of long-standing interest and a challenge for organic chemists because of the importance of these compounds in chemistry and biology. In particular, 1,5-disubstituted tetrazoles are very useful compounds in medicinal chemistry and important synthetic intermediates. [1, 2] In the past several decades, some general strategies for the synthesis of 1,5-disubstituted tetrazoles from functionalized starting materials have been developed (Scheme 1). These methods include: a) the reactions of ketones [3] or oximes [4] with sodium azide and hydrogen azides, b) the reactions of amides with sodium azides in the presence of phosphorus(V) chloride or triflic anhydride and [5] the reactions of amidrazones with dinitrogen tetroxide or nitrous acid, [6] c) the reactions of imidoyl chlorides [7a] or imidoylbenzotriazoles [7b] with sodium azides and, d) the reactions of nitriles with alkyl azides. [8] These developed methods significantly improved the synthesis of tetrazoles, but these approaches have some limitations, such as the use of protic acid catalysts, tedious workups, and the use of functionalized starting materials, hence encouraging scientists to discover new strategies.The direct transformation of hydrocarbon molecules by transition-metal-catalyzed selective CÀH and CÀC bond activation (cleavage) has attracted considerable attention, owing not only to its fundamental scientific appeal but also to its potential utility in organic synthesis. [9,10] A direct approach to tetrazoles through C À H and C À C bond cleavages of simple hydrocarbon molecules is still an extremely attractive yet challenging goal. Herein, we demonstrate a novel and efficient Cu-promoted implanting of nitrogen into simple hydrocarbon molecules to construct 1, 5-disubstituted tetrazoles through C À H and C À C bond cleavages, and C À N bond formation under mild and neutral reaction conditions (Scheme 1 e).Azide has been widely used as a useful aminating reagent in organic synthesis. [11,12] The application of azides for the direct synthesis of aryl nitriles [13] and alkenyl nitriles [13c-d] through C À H bond cleavage has been recently reported. Recent achievements on the functionalization of C À H and C À C bonds [9][10] encouraged us to try the direct synthesis of Scheme 1. Strategies for the preparation of 1,5-disubstituted tetrazoles. Bt = benzotriazole. Table 1: The direct transformation of (E)-1,3-diphenylprop-1-ene (1 a) into (E)-1-phenyl-5-styryl-1H-tetrazole (2 a). [a] Entry Catalyst (mol %) TMSN 3 (equiv) Oxidant (equiv) Yield [%] [b]

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“…Professor Ma and coworkers have reported oxetane ring expansions using 2-imino oxetanes decorated with both an alkyne and a carboxylate at the 4-position (Scheme 39) [52]. When these unusual oxetane precursors are treated with Bronsted acids (TfOH or TsOH), maleimide products are formed.…”

Section: Oxetane Ring Expansionsmentioning

confidence: 99%

Ring Expansions of Oxiranes and Oxetanes

Smith

Njardarson

2015

Topics in Heterocyclic Chemistry

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This chapter is focused on recently published (2006)(2007)(2008)(2009)(2010)(2011)(2012)(2013)(2014) oxirane and oxetane ring-expansion reactions. The majority of these advances employ oxirane substrates, the discussion of which is broken into five thematic sections representing insertions, cascades, metal-free, metal-catalyzed, and miscellaneous strategies. Oxetane ring-expansion reactions are still rare and are discussed together in one section. A concise graphical summary has been created for every new contribution to this area, highlighting reagents, reaction conditions, scope, mechanistic proposals, and asymmetry where applicable. This review chapter should enable researchers new to the field to quickly assess the current state of the art.

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Three‐Component Assembly and Divergent Ring‐Expansion Cascades of Functionalized 2‐Iminooxetanes

Cited by 91 publications

References 66 publications

Silver‐Catalyzed Nitrogenation of Alkynes: A Direct Approach to Nitriles through CC Bond Cleavage

Silver‐Catalyzed Nitrogenation of Alkynes: A Direct Approach to Nitriles through CC Bond Cleavage

Implanting Nitrogen into Hydrocarbon Molecules through CH and CC Bond Cleavages: A Direct Approach to Tetrazoles

Ring Expansions of Oxiranes and Oxetanes

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