Activated Nitriles in Heterocyclic Synthesis: Novel Syntheses of Pyrrolo[1,2-<i>c</i>]imidazole and Pyrano[2,3-<i>d</i>]imidazole Derivatives

Daboun, H. A.; Abdou, Sadek E.; Hussein, Mona Mustafa; Elnagdi, Mohamed Hilmy

doi:10.1055/s-1982-29857

Cited by 37 publications

(11 citation statements)

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“…Although a variety of derivatives of 4 are already known 8 and several synthetic approaches to such systems are already available a somewhat easy and efficient route to 4 (R¼3-indolyl or 2-pyrrolyl) has been reported recently by Slatt et al, 9 Elnagdi et al, 10 and Ibrahim et al 11 This attracted our attention as an efficient route to derivatives of 4. Thus, N,N-dimethylaniline 5a reacted readily with a mixture of acetic anhydride and cyanoacetic acid (thus producing 6 in situ) when heated at 80 C for 10 min to yield 7a in 80% yield.…”

Section: Resultsmentioning

confidence: 99%

Studies with enaminones and enaminonitriles: synthesis of 3-aroyl and 3-heteroaroyl-pyrazolo-[1,5-a]pyrimidines

et al. 2009

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Section: Resultsmentioning

confidence: 99%

Studies with enaminones and enaminonitriles: synthesis of 3-aroyl and 3-heteroaroyl-pyrazolo-[1,5-a]pyrimidines

et al. 2009

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“…Compound 27a was examined against hydroxylamine hydrochloride to yield a mixture of the aldoxime 61 and the aminoisoxazole derivatives 62 [99]. In contrast to the previously reported behaviour of 2-pyrazolin-5one [100], 2-thiazoline-4-one [101], and 2-thiohydantion derivatives [102], towards the action of arylidenemalononitrile, 3-phenyl-2isoxazolin-5-one 64 reacted with the cinnamonitrile derivative 63 to yield only the arylidene derivative 65 [103], as shown in Scheme 22. 3-Oxime-4-phenyl-1(H)-1,5-benzodiazepin-2-one 66 was allowed to react with different arylidenenitriles in the presence of triethylamine and yielded spirobenzodia-zepine isoxazole derivatives 67 and 68, as outlined in Scheme 23 [104].…”

Section: Scheme 20mentioning

confidence: 99%

“…These products rearrange on heating in aqueous ethanol into the thermodynamically stable dihydropyridines 248. Observed [100,101,151] dependency of the products of reactions of active methylene reagents with cinnamonitrile derivatives on the nature of reactants and reaction conditions has been reported [134,[226][227][228][229][230][231][232][233][234][235][236], as outlined in Scheme 86. Gewald et al [237] have shown that the product of reaction of 56 and 111 with trichloroacetonitrile are really the pyridine derivatives 256 and 257, respectively.…”

Section: Scheme 77mentioning

confidence: 99%

The Chemistry of Alkenyl Nitriles and its Utility in Heterocyclic Synthesis

Elgazwy¹

2013

Organic Chem Current Res

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including purines [7,8], pyrimidines [9], pyrazines [10] (some which are widely employed in the fluorescent dye industry [11]), imidazoles [12], biphenylenes [13], porphyrazines (which have great potential in optical sensor technology) [14] and diimines that are used as catalysts [15]. This review highlights the alkenyl nitrile chemistry with the focus on the utility of heterocyclic compounds. The synthesis and chemistry of the highly strained aryl nitrile is also briefly reviewed [16]. Heterocycles are ubiquitous in all kind of compounds of interest, and among all the possible synthetic methods of achieving their introduction into an structure, probably the use of a alkenyl nitrile analogue is the most direct one. The present review deals with the generation and synthetic uses of alkenyl nitriles and aryl nitriles formed in heterocyclic synthesis, and can be considered as an update of our revision published in 2007 on this topical [17]. Therefore, only references published from the second quarter of 2003 until the third quarter of 2010 are included, and the same restrictions to the literature coverage applied. Thus, only heterocycles compounds which are found applicability are considered. As previously, the present review is organized by the type of ring members and subdivided by the type of heterocycles fused compounds, including methods for their preparation and their synthetic uses. New developments in the utilities of some alkenyl nitriles in heterocyclic synthesis are reviewed. General synthetic routes based on the utilization of alkenyl nitriles of active imines are discussed. The major methods and modifications are analyzed [18-21]. In this review, which covers the literature up to date, we describe the new and improved methods for the construction of the skeletons, with a particular emphasis on the four, five and six membered ring of heterocyclic compounds. Some of these procedures have clear technical advantages over older methods in terms of yield and versatility, but do not employ new chemistry in the construction of the ring systems. The

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“…Neki 5-arilmetilen derivati se primenjuju kao korisni sintetički intermedijeri (šeme 9 i 10) [26,27].…”

Section: Reakcije Na C-5unclassified

Hydantoins: Synthesis, properties and anticonvulsant activity

Trišović¹,

Ušćumlić²,

Petrović³

2009

Hem Ind

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Hydantoin is a five-membered cyclic ureide that is present in numerous biologically active compounds including antiarrhytmics, anticonvulsants and antitumor agents. This paper describes different ways of synthesis of hydantoin-derivatives, their physical properties and reactivity. Also, the most widely used hydantoin anticonvulsants and the analysis of structureactivity relationships of anticonvulsant drugs in terms of lipophilicity and hydrogen bonding are presented here

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Activated Nitriles in Heterocyclic Synthesis: Novel Syntheses of Pyrrolo[1,2-c]imidazole and Pyrano[2,3-d]imidazole Derivatives

Cited by 37 publications

References 0 publications

Studies with enaminones and enaminonitriles: synthesis of 3-aroyl and 3-heteroaroyl-pyrazolo-[1,5-a]pyrimidines

Studies with enaminones and enaminonitriles: synthesis of 3-aroyl and 3-heteroaroyl-pyrazolo-[1,5-a]pyrimidines

The Chemistry of Alkenyl Nitriles and its Utility in Heterocyclic Synthesis

Hydantoins: Synthesis, properties and anticonvulsant activity

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