190365-96-9Relevant academic research and scientific papers
Metal chelation aptitudes of bis(o-azaheteroaryl)methanes as tuned by heterocycle charge demands
Abbotto, Alessandro,Bradamante, Silvia,Facchetti, Antonio,Pagani, Giorgio A.
, p. 5753 - 5772 (2002)
We describe the synthesis of a number of 1,3-azol-2-yl-, 1,3-benzazol-2-yl-, and azinyl-based bis- (o-azaheteroaryl)methanes (LH, L- = Het2CH-) and their coordinating properties toward divalent transition metals (Zn, Cu, Co, Ni, Hg,
The phenomenon of intramolecular attractive S...O interactions: Synthesis and structure of (1,10-phenanthroline)copper(II) complexes with isonitroso-(4-methylthiazol-2-yl)acetamide and isonitroso-(4-methylthiazol-2-yl)-(benzothiazol-2-yl)methanide
Domasevitch, Konstantin V.,Ponomareva, Vera V.,Mokhir, Andrey A.,Rusanov, Eduard B.,Sieler, Joachim,Hoyer, Eberhard
, p. 323 - 330 (1997)
Isonitroso-(4-methylthiazol-2-yl)acetamide H(L1), isonitroso-(4-methylthiazol-2-yl)(benzothiazol-2-yl)methanide H(L2) and their copper(II) complexes of composition [Cu(Phen){L1}(ClO4)] (1) and [Cu(Phen){L2}Cl]*C2H5OH (2) have been prepared. Crystal and molecular structures of the complexes have been determined from X-ray diffraction data (1: monoclinic, space group P21/c, with a = 11.611(2), b = 10.259(2), c = 17.869(4) A, β = 104.67(3)°, V = 2059.1(7) A3, Z = 4; R1 = 0.046 for the 2522 unique reflections with I > 2σ(I). 2: triclinic, space group P1, with a = 8.351(1), b = 10.876(1), c = 14.891(2) A, α = 96.170(8)°, β = 94.201(9)°, γ = 106.721(9)°, V = 1280.1(2) A3, Z = 2; R1 = 0.034 for the 4038 unique reflections with I > 2σ(I)). In the structure of 1 the coordination polyhedron of Cu2+ is a distorted square pyramid with an oxygen atom of the ClO4 counter anion in the apex (Cu-O 2.505(3) A); in complex 2 the copper atom adopts fivefold coordination of a slightly distorted trigonal-bipyramidal geometry with a chlorine atom in the equatorial plane (Cu-Cl 2.3504(9) A). Ethanol of crystallization gives rise to a hydrogen bond at the chlorine atom. In both structures the oximic anions are coordinated to the metal center in a bidentate chelate manner via the nitrogen atom of the nitroso group and the carbonyl oxygen atom (1) or via the benzothiazole nitrogen atom (2) (Cu-O, Cu-N in the range 1.963(2) - 2.031 (2) A). The thiazole group of the ligands takes no part in the coordination. The nitroso oxygen atoms possess short intramolecular contacts with thiazole sulphur atoms, with d〈S...O〉 at 2.605(3) (1) and 2.676(3) A (2), which may be attributed to a strong intraligand interaction.
Some reactions of 2-cyanomethyl-1,3-benzothiazole with expected biological activity
Hassan
experimental part, p. 2856 - 2869 (2010/04/30)
New pyrido[2,1-b]benzothiazoles 2a,b, 3, 2-aminoquinoline 4, coumarin 5, cyclohexane 6a,b, and 2-(1,3-benzothiazol-2-yl) methylidene 7 derivatives have been prepared via the reaction of 2-cyanomethyl-1,3-benzothiazole 1 with ,-unsaturated nitriles, α-chloro ethyl acetoacetate, 2-amino benzaldehyde, 5-chlorosalicylaldehyde, α,β-unsaturated ketone, and 2-aminobenzothiol hydrochloride. 2-Thiazole derivatives 9a,b were prepared from compound 1, which was converted to thioamide derivative 8 by reaction with HCl and thioacetamide, and cyclization of this thioamide with α-halogenated ketone gave 9a,b. Reaction of compound 1 and ethylacetate to afford ketonitrile 10. Treatment of 10 with hydrazine hydrate afforded aminopyrazole derivative 11. Substituted 4-aminothiophene 13 has been synthesized by reaction of compound 1 with p-chlorophenyl isothiocyanate. The resulting product 12 was then alkylated with phenacylbromide. Phenyl-2-yl-carbonylhydroximoyl-chloride 15 was prepared by treatment of the corresponding sulfonium bromide with sodium nitrite and hydrochloric acid in dioxane. Compound 15 reacted with α-(1,3- benzothiazol-2-yl) cinnamonitrile 14 afforded the isoxazole derivatives 16. Reaction of coumarin derivative 5 with anthranilamide, pyrimidine diamine, thiosemicarbazide, acetylacetone, and hydrazine hydrate yielded quinazoline-2-one 17, purine 18, triazole 19, 2-acetyl naphthalene-2-one 20, and N-aminoquinoline-2-one 21 derivatives.
2-(1,3-Benzothiazol-2-yl)ethanethioamides in Heterocyclic Synthesis: Novel Synthesis of Pyridine, Pyridopyrimidine, Coumarin, Thiazolone and Triazole Derivatives
Elneairy, Mohamed A. A.,Abdel-Rahman, Taha M.,Hammad, Ahmed M.
, p. 2834 - 2849 (2007/10/03)
The utility of 2-(1,3-benzothiazol-2-yl)ethanethioamide in the synthesis of several new pyridine, coumarin, pyridopyrimidine, thiazolone and triazole derivatives is reported.
