Acid Hydrazides, Potent Reagents for  Synthesis of Oxygen-, Nitrogen-, and/or Sulfur-Containing Heterocyclic Rings

Majumdar, Poulomi; Pati, Anita; Patra, Malay; Behera, Ratikanta; Behera, Ajaya Kumar

doi:10.1021/cr300122t

Cited by 264 publications

(124 citation statements)

References 306 publications

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“…367,368 These natural products exhibit a wide range of bioactivities including antidepressant, antiinflammatory, antiproliferative, antibacterial, and antifungal. 14,367 …”

Section: N–n Bond Forming Enzymesmentioning

confidence: 99%

“…9,10,499,500 There are many synthetic methods available for constructing these various 5- and 6-membered scaffolds. 14 As noted in previous sections, synthetic methods for constructing various N–N bond containing functional groups commonly utilize reagents in which this linkage is pre-formed. Methods for constructing heterocycles that involve direct N–N bond formation are rare, yet desirable due to the drawbacks of working with hydrazine.…”

Section: N–n Bond Forming Enzymesmentioning

confidence: 99%

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Heteroatom–Heteroatom Bond Formation in Natural Product Biosynthesis

et al. 2017

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Natural products that contain functional groups with heteroatom-heteroatom linkages (X–X, where X = N, O, S, and P) are a small yet intriguing group of metabolites. The reactivity and diversity of these structural motifs has captured the interest of synthetic and biological chemists alike. Functional groups containing X–X bonds are found in all major classes of natural products and often impart significant biological activity. This review presents our current understanding of the biosynthetic logic and enzymatic chemistry involved in the construction of X–X bond containing functional groups within natural products. Elucidating and characterizing biosynthetic pathways that generate X–X bonds could both provide tools for biocatalysis and synthetic biology, as well as guide efforts to uncover new natural products containing these structural features.

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“…367,368 These natural products exhibit a wide range of bioactivities including antidepressant, antiinflammatory, antiproliferative, antibacterial, and antifungal. 14,367 …”

Section: N–n Bond Forming Enzymesmentioning

confidence: 99%

Section: N–n Bond Forming Enzymesmentioning

confidence: 99%

Heteroatom–Heteroatom Bond Formation in Natural Product Biosynthesis

et al. 2017

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“…The synthetic strategy adopted to obtain the target products involves the conversion of methyl 3-heteroarylpropanoates 2a-d to key intermediate hydrazides 3a-d by refluxing with hydrazine hydrate in ethanol, a well-described procedure for diverse ester substrates. 22 These hydrazides were reacted with trialkylorthoesters (orthoformate, orthoacetate, and orthobenzoate) to obtain 5-[2-(trifluoromethylheteroaryl)-ethyl]-1,3,4-oxadiazoles (4-6) under mild conditions without other solvent (Table 1, Scheme 2). 23 Initially, the cyclocondensation between 3c and triethyl orthoacetate was carried out in ethanol reflux at a 1:1 stoichiometric ratio for 24 h, leading to a mixture of product 5c and reagents.…”

Section: Resultsmentioning

confidence: 99%

Strategies for the Efficient Synthesis of Biheterocyclic 5-[2-(Trifluoromethylheteroaryl)-ethyl]-1,3,4-oxadiazoles from Levulinic Acid

Malavolta

Frigo

Moura

et al. 2017

J. Braz. Chem. Soc.

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The synthesis of 5-[2-(trifluoromethylheteroaryl)-ethyl]-1,3,4-oxadiazoles derived from levulinic acid is reported. Cyclocondensations [4 + 1] between four different 5- [2-(trifluoromethylheteroaryl) propionylhydrazides derived from methyl 7,7,7-trifluoro-4-methoxy-6-oxo-4-heptenoate obtained from levulinic acid, and electrophilic orthoesters RC(OR 1 ) 3 (where R = H, Me, Ph) and CS 2 were carried out in a mild medium. Good yields (69-96%) of isolated products were obtained. The structures of the new ethylene-spaced biheterocycles were characterized using 1 H and 13 C nuclear magnetic resonance (NMR) spectroscopy and electrospray ionization coupled to tandem mass spectrometric (ESI MS/MS) data.

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“…Functionalized heterocycles are important compounds owing to their high potential biological activities. The fact that heterocycles are present in the structure of many drugs reflects the increasing attention to the synthesis of their new derivatives . Among the various heterocyclic compounds, 4‐oxo‐2‐thioxo‐1,3‐thiazinanes were less investigated, may be owing to the lack of enough procedures for the synthesis of these compounds.…”

Section: Introductionmentioning

confidence: 99%

Investigation of the Reaction of In Situ Prepared Dithiocarbamic Acids with Itaconic Anhydride in Water

Halimehjani

Nosood

2017

Journal of Heterocyclic Chem

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An environmentally benign procedure for the synthesis of 2‐(3‐alkyl‐4‐oxo‐2‐thioxo‐1,3‐thiazinan‐5‐yl)acetic acid via the one‐pot three‐component reaction of primary amines, carbon disulfide, and itaconic anhydride in water is described. Also, this protocol was expanded for the synthesis of succinic acids containing a dithiocarbamate group by using hindered primary amines and secondary amines.

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Acid Hydrazides, Potent Reagents for Synthesis of Oxygen-, Nitrogen-, and/or Sulfur-Containing Heterocyclic Rings

Cited by 264 publications

References 306 publications

Heteroatom–Heteroatom Bond Formation in Natural Product Biosynthesis

Heteroatom–Heteroatom Bond Formation in Natural Product Biosynthesis

Strategies for the Efficient Synthesis of Biheterocyclic 5-[2-(Trifluoromethylheteroaryl)-ethyl]-1,3,4-oxadiazoles from Levulinic Acid

Investigation of the Reaction of In Situ Prepared Dithiocarbamic Acids with Itaconic Anhydride in Water

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