A novel isocyanide-based three-component reaction: a facile synthesis of substituted 2H-pyran-3,4-dicarboxylates

Khalilzadeh, Mohammad A.; Hossaini, Zinatossadat; Baradarani, Mohammad Mehdi; Hasannia, Adel

doi:10.1016/j.tet.2010.08.041

Cited by 29 publications

(12 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These results further indicated that the microwave irradiation synthesis is a very effective method of building heterocyclic structures. The structures of all new compounds 4a~4n and 6a~6d were fully confirmed by means of IR, 1 H NMR, 13 C NMR and HRMS measurements .…”

Section: Introductionmentioning

confidence: 75%

“…The materials of the structural characterization with of 1 H NMR, 13 C NMR and IR for this article are available online at the supplementary materials.…”

Section: Supplementary Materialsmentioning

confidence: 99%

“…Consequently, a number of synthetic strategies for the construction of pyranopyran derivatives have been reported. [12][13][14][15][16] However, the conventional multistep methods for the preparation of complex compounds result in synthetic inefficiency and the generation of large amounts of wastes because of complicated synthetic operations including extraction and purification in every step. Furthermore, many preparations of these compounds require long reaction times, [17][18] harsh reaction conditions, 19 and/or expensive catalysts or reagents.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Convenient multicomponent reaction synthesis of novel pyrano[4,3-b]pyran derivatives via a domino reaction under microwave irradiation

Mao¹,

Wang²,

Zhang³

et al. 2016

Arkivoc

View full text Add to dashboard Cite

Novel pyrano [4,3-b]pyran-5-one derivatives have been obtained efficiently in a multicomponent domino cyclisation via the one-pot three-component reaction of aromatic aldehyde, 4-hydroxy-6-methyl-2-pyrone and N-methyl-1-(methylthio)-2-nitroethenamine in ethanol under microwave irradiation. The combined methods show excellent advantages such as higher yield, shorter reaction time and cleaner reaction, compared with conventional heating methods. The synthesized compounds are confirmed by 1 H NMR, 13 C NMR, IR and ESI-MS.

show abstract

Section: Introductionmentioning

confidence: 75%

“…The materials of the structural characterization with of 1 H NMR, 13 C NMR and IR for this article are available online at the supplementary materials.…”

Section: Supplementary Materialsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Convenient multicomponent reaction synthesis of novel pyrano[4,3-b]pyran derivatives via a domino reaction under microwave irradiation

Mao¹,

Wang²,

Zhang³

et al. 2016

Arkivoc

View full text Add to dashboard Cite

show abstract

“…21 As a useful synthon, organic dithiocarbamates have been extensively used for the synthesis of structurally diverse biological potent scaffolds such as isothiocyanates, 22 thiourea, 23 cynamide, 24 dithiobenzophene, 25 glycosides, 26 amide, 27 dicarboxylates, 28 benzimidazole, 29 carbamate, 30 pyran, 31 flavonoids 32 etc. In view of their tremendous importance and wide applications, their syntheses have gained considerable attention, and therefore have become a focus of synthetic organic chemistry.…”

Section: Etcmentioning

confidence: 99%

Triton-B catalyzed, efficient and solvent-free approach for the synthesis of dithiocarbamates

Zaidi¹,

Chaturvedi²,

Singh³

et al. 2017

10.5267/j.ccl

View full text Add to dashboard Cite

A novel one-pot, solvent-free method for the synthesis of dithiocarbamates was developed through the reaction of corresponding alkyl halides, amines and carbon disulfide employing catalytic amount of benzyl trimethyl ammonium hydroxide (Triton-B). The reaction conditions are milder with extremely simple work-up procedures than the reported methods, afforded high yields (82-98%) of the desired products.

show abstract

“…Organic dithiocarbamates have been extensively used as intermediate for the synthesis of structurally diverse synthetic intermediates/molecules of biological significance like antimalarial [11], anticholinergic [12], antimicrobial [13], antimitotic [14], antitubercular [15], antifungal [16], anticancer [17], antioxidant [18], antiprotozoal [19], antileprosy [20], antifolates [21], antitubulin [22], antialzheimer [23], anti-HIV [24], antipoliferative [25] and anticontraceptives [26] active agents. As a useful synthon organic dithiocarbamates have been extensively used for the synthesis of structurally diverse biological potent synthetic intermediates/molecules like isothiocyanates [27], thiourea [28], cynamide [29], dithiobenzophene [30], glycosides [31], β-sulphonamides [32], amide [33], dicarboxylates [34], thiadizoles [35], dithiolanes [36], and anhyd. K 2 CO 3 (10 eqv.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Dithiocarbamates of ω-Substituted (2-naphthyloxy)alkanes

et al. 2019

View full text Add to dashboard Cite

A series of dithiocarbamates of ω-substituted (2-naphthyloxy) alkanes was developed through condensation of 2-(2-chloro-alkoxy)naphthalene to various kinds of aliphatic, aromatic, alicyclic, heterocyclic primary and secondary amines employing benzyl trimethyl ammonium hydroxide in catalytic quantity (Triton-B/CS2 system) afforded desired products in high yields (82-98 %). The complete series of synthesized compounds (4-48) were evaluated for antimicrobial activity through microdilution method using various bacterial and fungal strains. The antifungal and antibacterial values were estimated as MIC values. Fluconazole and ciprofloxacin [16 to 0.03 µg/ mL] were used as the standard antifungal and antibacterial drug, respectively. Out of series of evaluated compounds, some of these compounds such as compounds 28, 29, 30, 31, 32, 33 have displayed maximum potency which is comparable to standard drugs.This is an open access journal, and articles are distributed under the terms of the Attribution 4.0 International (CC BY 4.0) License. This license lets others distribute, remix, tweak, and build upon your work, even commercially, as long as they credit the author for the original creation. You must give appropriate credit, provide a link to the license, and indicate if changes were made. thiones [37], benzimidazole [38], carbamate [39], pyran [40] and flavonoids [41], etc. Apart from above mentioned activities, dithiocarba-mates of various imidazole [42], brassinin [43], rhodanine [44], quinoline [45], metal complexes [46], ammonium salts [47], etc. derivative have emerged as potent antimicrobial agents. As our group is working in drug discovery through design and synthesis of novel class of natural/semi-synthetic/ synthetic molecules especially molecules like carbamates, dithiocarbamates, dithiocarbazates, etc.

show abstract

A novel isocyanide-based three-component reaction: a facile synthesis of substituted 2H-pyran-3,4-dicarboxylates

Cited by 29 publications

References 21 publications

Convenient multicomponent reaction synthesis of novel pyrano[4,3-b]pyran derivatives via a domino reaction under microwave irradiation

Convenient multicomponent reaction synthesis of novel pyrano[4,3-b]pyran derivatives via a domino reaction under microwave irradiation

Triton-B catalyzed, efficient and solvent-free approach for the synthesis of dithiocarbamates

Synthesis and Antimicrobial Activity of Dithiocarbamates of ω-Substituted (2-naphthyloxy)alkanes

Contact Info

Product

Resources

About