The efficient synthesis of Hantzsch 1,4-dihydropyridines via metal-free oxidative C C coupling by HBr and DMSO

Rezaei, Narjes; Ranjbar, Parviz Rashidi

doi:10.1016/j.tetlet.2018.10.010

Cited by 15 publications

(5 citation statements)

References 58 publications

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“…A facile synthesis of Hantzsch 1,4-dihydropyridines utilizing a HBr/DMSO reaction system was established by Ranjbar and coworker ( Scheme 31 ) [ 44 ]. A variety of substituted benzyl alcohols could be compatible to produce 1,4-dihydropyridines in excellent yields (14 examples, 92–97% yield).…”

Section: Dmso As the Oxidantmentioning

confidence: 99%

Recent Advances in DMSO-Based Direct Synthesis of Heterocycles

Cui

2022

Molecules

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Besides serving as a low-toxicity, inexpensive and easily accessible solvent, dimethyl sulfoxide (DMSO) has also been extensively used as a versatile reagent for the synthesis of functionalized molecules. Dimethyl sulfoxide can not only be utilized as a carbon source, a sulfur source and an oxygen source, but also be employed as a crucial oxidant enabling various transformations. The past decade has witnessed a large number of impressive achievements on the direct synthesis of heterocycles as well as modifications of heterocyclic compounds by applying DMSO as a reagent. This review summarized the DMSO-based direct heterocycle constructions from 2012 to 2022.

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Section: Dmso As the Oxidantmentioning

confidence: 99%

Recent Advances in DMSO-Based Direct Synthesis of Heterocycles

Cui

2022

Molecules

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“…have discussed novel and proficient one‐pot preparation of Hantzsch 1,4‐dihydropyridines in admirable yields at 75 °C through the three‐component reaction of benzyl alcohols, alkyl acetoacetate and ammonium hydroxide by grouping of HBr and DMSO (Dimethyl sulfoxide) via the metal‐free oxidative C−C coupling (Scheme 15). This presented protocol uses the benzyl alcohols as a replacement of aldehydes as a new variation of the Hantzsch reaction [24] . In presented protocol Benzylic alcohols were fruitfully activated by virtue of BDMS which is generated in situ by the reaction of HBr and DMSO.…”

Section: Bromodimethylsulfonium Bromide (Bdms) As a Catalystmentioning

confidence: 99%

“…This presented protocol uses the benzyl alcohols as a replacement of aldehydes as a new variation of the Hantzsch reaction. [24] In presented protocol Benzylic alcohols were fruitfully activated by virtue of BDMS which is generated in situ by the reaction of HBr and DMSO. Several of the key features of this route are less reaction times, easy work-up, no formation of side products, excellent yield of the required product and use of stable benzylic alcohols in position of aldehydes in the Hantzsch 1, 4dihydropyridine synthesis.…”

Section: Synthesis Of Hantzsch Productsmentioning

confidence: 99%

The Role of (BDMS) Bromodimethylsulfonium bromide as a Catalyst and Brominating Reagent: A Concise Overview

2022

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Bromodimethylsulfonium bromide (BDMS) is an expedient storage of molecular bromine or bromine radicals or bromonium ions and also of nucleophilic bromide ion. It is an easily available, inexpensive and versatile reagent. It is used as an effective brominating reagent as well as a valuable catalyst for several organic conversions. The prominent characteristics of this compound are the straight forwardness of the process, the ease of access of the compound, no requirement of chromatographic separation, no additional base, Lewis acid, or any other catalyst, better yields in comparatively less reaction times and assist to maintain the stoichiometric ratio during the reactions. The present article includes the catalytic applications as well as its brominating role in organic reactions.

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“…By using HBr in DMSO, the three‐component treatment of 1 equivalent of benzylic alcohols 60 , 2 equivalents of 1,3‐dicarbonyls 61 , and 1 equivalent of ammonium hydroxide 62 at 75 °C furnished the desired 1,4‐dihydropyridine products 63 in 92–97 % yield within 2.5 hours (Scheme 29). [51] This metal‐free oxidative reaction was accelerated through the activation of benzylic alcohol by in situ generated bromodimethylsulfoniumbromide (BDMS) from HBr and DMSO. The exploitation of benzylic alcohols in place of aldehydes effectively works within a short period of time for the synthesis of 1,4‐dihydropyridine marks the key advantages of this approach.…”

Section: Synthesis Of 14‐dihydropyridines Via One‐pot Reactions Under...mentioning

confidence: 99%

Recent Advances and Prospects in the Transition‐Metal‐Free Synthesis of 1,4‐Dihydropyridines

et al. 2022

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The synthesis of novel nitrogen‐containing heterocycles as a result of their frequent existence in natural products, commercially available drugs, and optoelectronic materials is extremely demanding but challenging due to the involvement of toxic solvents, and sometimes transition‐metal catalyst(s) which are often associated with environmental safety concerns. 1,4‐dihydropyridine (1,4‐DHP), of synthetic and natural origin, are among one of the privileged classes of nitrogen‐containing heterocycles, representing a broad spectrum of pharmaceutical properties, and has received considerable interest in medicinal and synthetic organic chemistry. Recognizing the prominent significance of this structural motif, substantial efforts have been paid not only for their expedient synthesis but also for the discovery of novel complex molecules by using them as key active building blocks. However, developing elegant synthetic processes provides effortless access to 1,4‐dihydropyridines by exploring environmentally friendly conditions with the primary goal of lowering the expenditure of the overall process is extremely demanding but challenging. In this mini‐review article, we have demonstrated a clear presentation of the recent transition‐metal‐free catalyzed synthesis of 1,4‐dihydropyridines of potential therapeutic interests and covered the literature from 2015 to date.

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The efficient synthesis of Hantzsch 1,4-dihydropyridines via metal-free oxidative C C coupling by HBr and DMSO

Cited by 15 publications

References 58 publications

Recent Advances in DMSO-Based Direct Synthesis of Heterocycles

Recent Advances in DMSO-Based Direct Synthesis of Heterocycles

The Role of (BDMS) Bromodimethylsulfonium bromide as a Catalyst and Brominating Reagent: A Concise Overview

Recent Advances and Prospects in the Transition‐Metal‐Free Synthesis of 1,4‐Dihydropyridines

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