Untitled

Собенина, Л. Н.; Demenev, A. P.; Михалева, А. И.; Ushakov, Igor А.; Afonin, A. V.; D’yachkova, S. G.; Beskrylaya, E. A.; Опарина, Л. А.; Елохина, В. Н.; Volkova, K. A.; Петрова, О. В.; Трофимов, Б. А.

doi:10.1023/a:1014863511588

Cited by 9 publications

(6 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Heating pyrrole-2-carbodithionates 52 with anions of C-H acids generated from malononitrile or cyanoacetamide in KOH/DMSO (room temperature, 0.5 h). Interaction of the resulting enethiolates 53 with haloacetylenes 54 afforded the pyrrolothiazolidines 55, as outlined in Scheme 18 [86][87][88][89][90][91].…”

Section: Scheme 16mentioning

confidence: 99%

The Chemistry of Alkenyl Nitriles and its Utility in Heterocyclic Synthesis

Elgazwy¹

2013

Organic Chem Current Res

View full text Add to dashboard Cite

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

show abstract

Section: Scheme 16mentioning

confidence: 99%

The Chemistry of Alkenyl Nitriles and its Utility in Heterocyclic Synthesis

Elgazwy¹

2013

Organic Chem Current Res

View full text Add to dashboard Cite

show abstract

“…Sobenina et al showed previously in [268][269][270][271] that the range of application of pyrrole-2-carbodithioates 469a-d in fine organic synthesis might be broadened significantly due to their ability to react with CH-acids with the formation of functionally substituted 2-vinylpyrroles, which are key in- [272] investigated the interaction of 1-(2-pyrrolyl)vinylthiolates 471a-d, generated in situ from pyrrole-2-carbo-dithioates 469a-d and the methylene-reactive nitriles 472a,b in KOH-DMSO, with 2-benzoyl-1-bromoacetylene (473a), 1chloro-2-ethylthioacetylene (473b) and 2-(1-iodo-2-propynoxy)-1-methoxyethane (473c), as shown in Scheme 153.…”

Section: Benzo Derivatives Of a Six-membered Ring With One Heteroatommentioning

confidence: 99%

Utilities of Some Carbon Nucleophiles in Heterocyclic Synthesis

Madkour¹,

Elgazwy

2007

COC

View full text Add to dashboard Cite

New developments in the utilities of some carbon nucleophiles in heterocyclic synthesis are reviewed. General synthetic routes based on the utilization of carbon nucleophiles of active methylene are discussed. The major methods and modifications are analyzed. Heterocycles are ubiquitous in all kind of compounds of interest, and among all the possible synthetic methods of achieving their introduction into a structure, probably the use of a carbon nucleophile analogues are the most direct one. The present review deals with the generation and synthetic of carbon nucleophile, which uses as scaffold for the heterocyclic synthesis, and can be considered as an update review. Therefore the only references published upon the second quarter of 2003 are included, and the same restrictions to the literature coverage apply.

show abstract

“…95 Reaction of vinylthiolates 281, which are formed in situ from pyrrole-2-carbodithioates 264 and methylenoactive nitriles, with 2-benzoyl-1-bromo-and 2-chloro-1-ethylthioacetylenes 282a,b in the KOH-DMSO system affords functionalized pyrrolothiazoles 283a,b (Scheme 103). [97][98][99][100] Vinylthiolates 281 and bromobenzoylacetylene 282a stereoselectively form Z-isomers of pyrrolothiazoles 283a. The observed stereospecificity is likely caused by steric hindrances which do not allow formation of the E-isomer.…”

Section: Cyclization With Participation Of Functional Groupsmentioning

confidence: 99%

“…All steps of the synthesis of pyrrolothiazoles 283a,b are performed in a single reactor without isolation of intermediate products. [97][98][99][100] 2-and 3-Vinylpyrroles 285a react with NH-and N-methylglycinate to afford dipyrroles 286 with the 2,5-substituted pyrrole ring (Scheme 104). 101 When the chlorine atom in salt 285a is replaced by a dimethylamino group (the salt 285b), dipyrroles with a 2,3-disubstituted ring 287 are formed (Scheme 105).…”

Section: Cyclization With Participation Of Functional Groupsmentioning

confidence: 99%