Investigation of the Reaction of Chloroacetyl Chloride with 1,5-Benzothiazepines: Selective Synthesis of Azeto[2,1-d][1,5]benzothiazepines by Green Chemical Methods and Their Biological Activity

Benzo[1,5]thiazepine: Synthesis, Reactions, Spectroscopy, and Applications

“…good yield. Similarly, products 99b-f were obtained in fair to good yield [26] (Scheme 24). 103 in excellent yield.…”

“…The appearance of a sharp absorption band near 1620 cm −1 confirmed the presence of C=N group in the spectrum of (S, E)-2-(benzo[ ][1, 3]dioxol-5-yl)-4-phenyl-2,3-dihydrobenzo [1,5]thiazepine 94a [25]. 2-chloro-7-methoxy-1-oxo-2a-phenyl-2,2a,3,4-tetrahydro-1H-azeto[1, 2-]benzo [1,5]thiazepine-4-carboxylic acid 99a revealed in its IR spectrum two carbonyl bands at 1680 and 1725 cm −1 , beside a broad band for OH group around 3288 cm −1 and another band at 748 cm −1 which could be due to C-Cl oscillating frequencies [26]. The IR spectrum by spectroscopic studies.…”

“…Theoretically, compound 99a-f exhibiting two chiral centers could exist in two diastereomeric forms; however, the 1 H NMR spectra and chromatographic studies of the isolated compounds indicated the formation of only one diastereomer. For example, the PMR spectrum (CDCl 3 , 300.15MHz) of 2-chloro-7-methoxy-1-oxo-2a-phenyl-2,2a,3,4-tetrahydro-1H-azeto[1, 2-]benzo [1,5]thiaz-epine-4-carboxylic acid [26]. The 1 H NMR spectra of 107a-d, generally, showed the enamine methyl (-N-C=C-Me) group at 2.60-2.65 ppm, the NH group at 6.19-6.23 ppm and S-CH group at the C-2 position as a singlet at 5.89-6.14 ppm.…”

Convenient synthesis of novel pyrimido[4,5‐b][1,5]benzothiazepines

“…Among the privileged heterocyclic scaffolds, [1,5]benzothiazepines and fused [1,5]benzothiazepines were on the scope of chemists efforts for several years. [1,2] These compounds have been described as Calcium channel blockers, [3][4][5][6] hypotensive, [7][8][9][10] drugs of liver diseases, [11,12] antidepressants, [13][14][15] anticholinesterase inhibitors, [16][17] anticancer, [18][19][20][21][22][23] diuretics, [24] antimicrobials, [25][26][27][28][29][30][31][32][33][34][35][36][37][38] anti HIV, [39][40][41] and antituberculosis [42,43] agents. The useful procedures for the preparation of 1,5-benzothiazepines are mainly based on the condensation of 2-aminobenzenethiol with α,β-unsaturated ketones.…”