scholarly journals Ferrocenyl imidazolo[2,1-b]-1,3,4-thiadiazoles: A microwave-assisted catalyst-free synthesis, characterization, and biological activities

2020 ◽  
pp. 174751982093990
Author(s):  
Yuting Liu ◽  
Lan Yang ◽  
Dawei Yin
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Biological Activities ◽  
Low Cost ◽  
Microwave Assisted ◽  
Catalyst Free ◽  
Alkyl Groups ◽  
13C Nuclear Magnetic Resonance ◽  
1H Nuclear Magnetic Resonance ◽  
Nuclear Magnetic

Ferrocenyl imidazolo[2,1- b]-1,3,4-thiadiazoles are synthesized using 2-amino-5-substituted-1,3,4-thiadiazole and α-bromoacetyl ferrocene as substrates under microwave-assisted and catalyst-free conditions. The structures are characterized by infrared, 1H nuclear magnetic resonance, 13C nuclear magnetic resonance, mass spectrometry, and elemental analysis. Compared with conventional methods, the present protocol has the advantages of being rapid, efficient, environmentally friendly, and low cost. The results of biological activity studies showed that the products displayed better activities than those of 2-amino-5-substituted-1,3,4-thiadiazole. The biological activities of compounds in which R = phenyl were better than those with alkyl groups. Compounds with electron-withdrawing groups on the aryl moiety showed increased biological activities.

1H and 13C Nuclear Magnetic Resonance Studies of the Hindered Phencyclone Adducts of Some Smaller Branched N-Alkyl Maleimides: Rigorous Aryl Proton Assignments with High-Resolution Two-Dimensional (COSY45) Spectroscopy, and Anisotropic Shielding Effects and Ab Initio Geometry Optimizations

2005 ◽  
Vol 59 (3) ◽  
pp. 354-365 ◽  
Author(s):  
Ronald Callahan ◽  
Ron Prip ◽  
Navroz Shariff ◽  
Olga Sklyut ◽  
Robert Rothchild ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
High Resolution ◽  
Basis Set ◽  
Nmr Studies ◽  
Alkyl Groups ◽  
13C Nuclear Magnetic Resonance ◽  
C Nmr ◽  
Shielding Effects ◽  
Nuclear Magnetic

Phencyclone, 1, a potent Diels-Alder diene, reacts with a series of N-alkylmaleimides, 2, to form hindered adducts, 3. The 300 MHz 1H and 75 MHz 13C NMR studies of these adducts at ambient temperatures have demonstrated slow rotations on the nuclear magnetic resonance (NMR) timescales for the unsubstituted bridgehead phenyl groups, and have revealed substantial magnetic anisotropic shielding effects in the 1H spectra of the N-alkyl groups of the adducts. The selected N-alkyl groups for the target compounds emphasized smaller branched alkyls, including C3 (isopropyl, a); C4 (isobutyl, b; and t-butyl, c); C5 (n-pentyl, d; isopentyl [isoamyl], e; 1-ethylpropyl, f; t-amyl, g;) and a related C8 isomer (1,1,3,3-tetramethylbutyl [“t-octyl”], h). The straight-chain n-pentyl analog was included as a reference. This present work on the branched N-alkylmaleimide adducts appreciably extends our earlier compilation on the N-n-alkylmaleimide adducts. Key methods for proton assignments included “high-resolution” 1H–1H chemical shift correlation spectroscopy, COSY45. 13C NMR of the adducts, 3, verified the expected number of aryl carbons for slow exchange limit (SEL) spectra of the bridgehead phenyl groups. The synthetic routes involved reaction of the corresponding amines, 4, with maleic anhydride to give the N-alkylmaleamic acids, 5, which underwent cyclodehydration to form the maleimides, 2. Magnetic anisotropic shielding magnitudes for alkyl group protons in the adducts were calculated relative to corresponding proton chemical shifts in the maleimides. Geometry optimizations for the above adducts (and for the N-n-butylmaleimide adduct) were performed at the Hartree-Fock level with the 6–31G* basis set. The existence of different contributing conformers for the adducts is discussed with respect to their calculated energies and implications regarding experimentally observed anisotropic shielding magnitudes.

scholarly journals Simple, novel, and efficient synthesis of ethyl 2-(2-(1H-indol-3-yl)benzo[d]thiazol-3(2H)-yl)-2-cyanoacetate or acetate via a three-component reaction

2020 ◽  
pp. 174751982095201
Author(s):  
Mahmoud Nassiri ◽  
Forough Jalili Milani
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Indole Derivatives ◽  
Efficient Synthesis ◽  
13C Nuclear Magnetic Resonance ◽  
Three Component Reaction ◽  
1H Nuclear Magnetic Resonance ◽  
Elemental Analyses ◽  
New Compounds ◽  
Nuclear Magnetic

Ethyl 2-(2-(1 H-indol-3-yl)benzo[ d]thiazol-3(2 H)-yl)-2-cyanoacetate or acetate 6a–f as a series of novel compounds were synthesized from the reactions of benzothiazole, 2-methylbenzothiazole, or 2,5-dimethylbenzothiazole and ethyl bromocyanoacetate with indole derivatives. The reactions proceeded in acetone as a solvent under reflux for 5 h in good yields. The structures of new compounds were confirmed by 1H nuclear magnetic resonance, 13C nuclear magnetic resonance, infrared, elemental analyses, and mass spectroscopy.

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