On the functionalization of benzo[e][2,1]thiazine

Abstract

SummaryThe reactions of benzo[e][2,1]thiazine-4-chloro-3-carbaldehydes 1 and benzo[e][2,1]thiazine-4-chloro-3-carbonitriles 2 with a number of oxidizing and reducing agents are reported. A number of new, highly functionalized benzo[e][2,1]thiazine derivatives having potential biological activity were synthesized and described.

3,3′-(Phenylmethylene)bis(1-ethyl-3,4-dihydro-1H-2,1-benzothiazine-2,2,4-trione): single-crystal X-ray diffraction study, quantum-chemical calculations and Hirshfeld surface analysis

“…It incorporates a -keto sultam fragment that allows a molecule to be a versatile synthetic intermediate used for the preparation of diverse molecular platforms (Ahmad et al, 2018;Grombein et al, 2015;D'Amico et al, 2007;Pieroni et al, 2012;Popov et al, 2010;Popov et al, 2009). Moreover, such a fragment is probably responsible for non-trivial reactivity as we have established previously (Lega et al, 2016c;Kolodyazhna et al, 2021).…”

Bioactive Thiazine and Benzothiazine Derivatives: Green Synthesis Methods and Their Medicinal Importance

“…The benzothiazepines conjugated with other thiazines were tested on neuronal receptors, where only one derivative showed inhibitory effects on the central nervous system while most of the others exhibited anti-inflammatory properties [78]. Benzothiazines are quite bioactive and this activity, mostly depends on the attached side groups [79,80]. The current oxicam medicines are chemically benzothiazines in nature (Figure 5) and they are second generation non-steroidal drugs that act as an anti-inflammatory agent [79,80].…”

“…Benzothiazines are quite bioactive and this activity, mostly depends on the attached side groups [79,80]. The current oxicam medicines are chemically benzothiazines in nature (Figure 5) and they are second generation non-steroidal drugs that act as an anti-inflammatory agent [79,80]. The current medicinal use of oxicams is restricted due to their adverse effects, although a number of research efforts were done to increase their potency against inflammatory conditions with lower side effects [79,80].…”

“…The current oxicam medicines are chemically benzothiazines in nature (Figure 5) and they are second generation non-steroidal drugs that act as an anti-inflammatory agent [79,80]. The current medicinal use of oxicams is restricted due to their adverse effects, although a number of research efforts were done to increase their potency against inflammatory conditions with lower side effects [79,80]. Xu et al resolved the crystal structure of cyclooxygenases in binding mode with oxicam compounds at 2–2.45 Å resolution [81,82].…”

Novel Benzothiazine Derivatives viaFormylation of 2,3‐Dihydro‐4H‐benzo[e][1,4]thiazin‐3‐on‐1,1‐dioxide

“…Resulting compounds (Fig. ), in particular, β‐chloroaldehydes 1 , β‐chloronitriles 2 , β‐aminovinylketones 3 , and hydroxymethyleneketones 4 were demonstrated to be the versatile intermediates in the synthesis of more elaborate benzothiazine derivatives .…”