One-pot, Three-component Synthesis of 7H-[1,3,4]Thiadiazolo[ 3,2-a]pyridines from 2-Phenacyl-[1,3,4]thiadiazole Derivatives and Arylmethylene-cyanoacetic Acid Derivatives

2007 ◽  
Vol 62 (10) ◽  
pp. 1298-1304 ◽  
Author(s):  
Imran Ali Hashmi ◽  
Wolfgang Frey ◽  
Ivo C. Ivanovc ◽  
Willi Kantlehner

Generally, arylmethylene-cyanoacetic acid derivatives react with enols and aromatic or heteroaromatic hydroxy compounds to afford 2-amino-4H-pyran derivatives of type 6. In contrast, a ring closure with the nitrogen atom of the thiadiazole ring occurs when 2-phenacyl-1,3,4-thiadiazoles (1a - d) act on derivatives of arylmethylene-cyanoacetic acid giving rise to the formation of 7H- [1,3,4]thiazolo[3,2-a]pyridine derivatives 5a - r. The same products are obtained if 2-phenacyl-1,3,4- thiadiazoles react with aromatic or heteroaromatic aldehydes and cyanoacetic acid derivatives. The constitution of the novel compounds 5 has been confirmed by an X-ray analysis of 5a.

1982 ◽  
Vol 35 (7) ◽  
pp. 1451 ◽  
Author(s):  
DW Cameron ◽  
KR Deutscher ◽  
GI Feutrill ◽  
DE Hunt

Synthesis of specific di- and tri-hydroxyazaanthraquinones by Friedel-Crafts procedures is limited by orientational ambiguity and by the lack of reactivity of pyridine derivatives in electrophilic acylation processes; however, suitable pyridines have been made to undergo radical benzoylation and benzylation at unsubstituted positions 2, 4 and 6. In particular, derivatives of pyridine-3-carbo-nitrile have been benzoylated at positions 2 and 4. Ring closure by intramolecular Houben-Hoesch reaction has then led to specifically substituted 1-and 2-azaanthraquinones and thence to the antibiotic bostrycoidin (1).


Catalysts ◽  
2019 ◽  
Vol 9 (12) ◽  
pp. 1000
Author(s):  
Iqbal ◽  
Sadiq ◽  
Sadiq ◽  
Ullah ◽  
Fazal ◽  
...  

A simple and practical procedure has been adopted for one pot synthesis of benzimidazole derivatives under mild reaction conditions, starting from cinnamyl alcohol (COH) with bimetallic nanoparticles (BNPs) and supported bimetallic nanoparticles of Cu, Ti, Zn, Mn, Ag, and Co. All the catalysts were characterized by Scanning Electron Microscopy (SEM), Energy Dispersive X-ray Spectroscopy (EDX), X-Ray Diffractometry (XRD), Brunauer Emmett-Teller (BET) surface area, and pore size analyzer. The products were identified/quantified with 1HNMR, FT-IR, and MS. 98% yield of substituted derivatives of benzimidazole was obtained with Cu–Ti supported on FMWCNTs in ethanol with excellent selectivity. Quantum chemical calculations of molecular reactivity of substituted cinnamaldehyde (CHO) and ortho phenylenediamine (OPD) have good consistency with experimental results. The returns of this work were the use of readily available catalysts, high yield, short reaction time, and simplicity of the process.


2012 ◽  
Vol 2012 ◽  
pp. 1-7
Author(s):  
Rafal Kruszynski ◽  
Tomasz Sieranski ◽  
Bartlomiej Lewinski ◽  
Agata Trzesowska-Kruszynska ◽  
Ewelina Czubacka

The reaction of molybdophosphoric acid with zinc carbonate followed by addition of hmta leads to formation of a triclinic polymorph of bis(3,5,7-triaza-1-azoniatricyclo[3.3.1.13,7]decane) bis(μ4-oxo)-tris(μ3-oxo)-nonakis(μ2-oxo)-nonaaqua-decaoxo-hepta-molybdenum-di-zinc(II) dihydrate in a one pot simple reaction. The obtained compound has been characterised by IR, UV-Vis spectroscopy, elemental analysis, and X-ray crystallography. A detailed comparison between both polymorphic forms: triclinic a=22.758 Å, b=24.702 Å, c=31.995 Å, α=101.206°, β=103.256°, γ=105.736°, and V=16203.8 Å3 and monoclinic a=43.120 Å, b=12.399 Å, c=16.285 Å, α=90.00°, β=111.12°, γ=90.00°, and V=8122 Å3 was performed. The influence of the synthesis procedure on polymorph formation was described.


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