Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-<i>N</i>-phenylacetamides

Liu, Weibing; Zhang, Qing; Zhu, Zhibo

doi:10.3762/bjoc.8.38

Cited by 21 publications

(15 citation statements)

References 39 publications

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“…Physical Data of Compounds 4: 4a1 – 4b1 , 4d1 , 4a2 – 4b2 and 4d2 – 4f2 are known compounds, and their analytical data are in good agreement with those reported in the literature 6e…”

Section: Methodssupporting

confidence: 84%

“…So far, many synthetic methodologies for α,α‐dihaloamides are available, among which the most prevalent strategy relies heavily upon the ammonolysis of α,α‐dihalocarboxylic acid derivatives with an amine 3,5. Other methods are reported by the direct α,α‐dihalogenation of β‐oxo amides with various halogenating systems, such as chlorine/ hv ,6a SO 2 Cl 2 ,6b N ‐chlorosuccinimide/NaH,6c aqueous bromine,6d and PhI(OAc) 2 /ZnX 2 (X = Cl, Br) 6e. Nevertheless, some of these methods involve hazardous reagents, harsh reaction conditions, or generation of wastes that not only reduce process efficiency but also pose environmental problems.…”

Section: Introductionmentioning

confidence: 99%

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Divergent Synthesis of α,α‐Dihaloamides through α,α‐Dihalogenation of β‐Oxo Amides by Using N‐Halosuccinimides

Wang

Zhang

et al. 2013

Eur J Org Chem

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An efficient and divergent one‐pot synthesis of α,α‐dihaloamides from readily available β‐oxo amides based on the selection of reaction conditions is reported. α,α‐Dihalo‐β‐oxo amides were produced by treating β‐oxo amides with N‐chlorosuccinimide (NCS) or N‐bromosuccinimide (NBS) in water at room temperature, whereas α,α‐dihaloacetamides were synthesized by subjecting β‐oxo amides to NCS or NBS in ethanol under reflux.

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“…Physical Data of Compounds 4: 4a1 – 4b1 , 4d1 , 4a2 – 4b2 and 4d2 – 4f2 are known compounds, and their analytical data are in good agreement with those reported in the literature 6e…”

Section: Methodssupporting

confidence: 84%

Section: Introductionmentioning

confidence: 99%

Divergent Synthesis of α,α‐Dihaloamides through α,α‐Dihalogenation of β‐Oxo Amides by Using N‐Halosuccinimides

Wang

Zhang

et al. 2013

Eur J Org Chem

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“…Thus, further halo-gen substitutions should be performed in order to reach the desired target. 10 Moreover, more complex routes involving tandem electrophilic α,α-dihalogenations-deacylations of acetoacetanilide derivatives have been reported (e.g., Reinshagen, 11 Liu-Zhu 12 and Li-Zhang 13 ) (Scheme 1). Laura Castoldi was born in 1986 in Pavia (Northern Italy): after an Erasmus placement at the Complutense University of Madrid in the group of Profs.…”

mentioning

confidence: 99%

Homologation of Isocyanates with Lithium Carbenoids: A Straightforward Access to α-Halomethyl- and α,α-Dihalomethylamides

et al. 2014

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Treatment of widely available isocyanates with monohalolithium and dihalolithium carbenoids provides a valuable protocol for the one-pot preparation of α-halo-and α,α-dihaloacetamide derivatives. While monohalolithium carbenoids can be prepared by a smooth lithium-halogen exchange, the preparation of the corresponding dihalo compounds proved to be highly dependent on the base used to realize the deprotonation, with lithium 2,2,6,6-tetramethylpiperidine emerging as optimal. The clear advantages of the procedure are: (a) broad scope of isocyanates that can be employed; (b) preservation of the optical purity when chiral materials are used; (c) divergent access to different haloamides by simply selecting the homologating agents. We also report an application of Charette's imidoyl triflate activation of a secondary amide to the synthesis of an α-chloro ketone and 15 N NMR data for selected compounds.

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“…In 2012, Wang et al., developed an efficient method to generate 4 b , from gem ‐dibromination of 1,3‐dicarbonyl compounds 5 b using ball‐mill mixing with the oxone and NaBr (Table , entry 2). In the same year, Liu and his co‐workers, synthesized 2,2‐ dihaloacetamides 4 c from 3‐oxo‐butanamides 5 c via dihalooxamide intermediate 4 c′ (Table , entry 3). This is a new fragmentation process for selective synthesis of α,α‐dihaloketones.…”

Section: Synthetic Approaches To αα‐Dihaloketonesmentioning

confidence: 99%

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

Sadhukhan

Santhi

Baire

2020

Chemistry A European J

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The α,α‐dihalocarbonyl moiety is a bifunctional system with a gem‐dihalocarbon and a carbonyl carbon in 1,2‐fashion. This is one of the privileged scaffolds in medicinal chemistry due to its chemical and metabolic stability and lipophilicity. They have also been found in numerous structurally divergent natural products and most of their fabricated structures have already been in medicinal use. Apart from their important use in medicinal chemistry, the α,α‐dihalocarbonyl groups have been employed as key building blocks for the development of novel synthetic strategies and utilized as intermediates in total synthesis. In addition to the traditional transformations such as oxidations, reductions, and C−C bond formations, recently several new and non‐classical reactions have also been developed. This review provides short description of existing methods for their synthesis and detailed discussion on the efforts for the discovery and development of new reactions by employing α,α‐dihaloketones as synthetic building blocks. We have presented their use as key functional groups for the synthesis of polycyclic systems of medicinal and material importance and natural products.

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Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-N-phenylacetamides

Cited by 21 publications

References 39 publications

Divergent Synthesis of α,α‐Dihaloamides through α,α‐Dihalogenation of β‐Oxo Amides by Using N‐Halosuccinimides

Divergent Synthesis of α,α‐Dihaloamides through α,α‐Dihalogenation of β‐Oxo Amides by Using N‐Halosuccinimides

Homologation of Isocyanates with Lithium Carbenoids: A Straightforward Access to α-Halomethyl- and α,α-Dihalomethylamides

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

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