Synthesis of 2‐oxo and 2‐thioxo‐3(2H)‐benzothiazoleethanimic acid anhydride with acetic acid and related products

Abstract

The reaction of the appropriate 2‐benzothiazolinone with 2‐chloroacetamide under basic conditions afforded the 2‐oxo‐3(2H)‐benzothiazolineacetamides 6–9. The 2‐thioxo‐3(2H)‐benzothiazolineacetamide (10) was prepared by the reaction of 3‐(carbethoxymethyl)benzothiazoline‐2‐thione with ammonium hydroxide. The reaction of acetamides 6–10 with the appropriate anhydride containing a catalytic amount of the sodium salt of the acid corresponding to the anhydride afforded the titled compounds 11–18 in excellent yields. The omission of the catalyst in the same reaction furnished a mixture containing 57% of the titled compound, 37% of the nitrile and 6% of an unknown. Possible mechanism and supporting nmr, ir and mass spectral data are discussed.

Retrograde sulfur flow from glucosinolates to cysteine in Arabidopsis thaliana

“…Subsequently, we explored the reactions that further convert RA into primary metabolites such as Cys. The 1,3-thiazolidin-2-thione ring in RA has a potential to release the ITC-derived sulfur atom via a sulfur–oxygen exchange reaction ( 42 ), producing 1,3-thiazolidin-2-one-4-carboxylic acid (procysteine, hereafter referred to as pCys) ( Fig. 4 A ).…”

6-Sulfonylbenzothiazolones as potential scaffolds for the design of 5-HT6 ligands

“…Benzothiazolone 1 reacted in 70% nitric acid to give 6-nitro benzothiazolone 8 [27,31], which was allowed to react in DMF with potassium carbonate and the corresponding 2-chloroethylalkylamine derivatives to yield compounds 9e11 with moderate yields (35e42%). Reduction of the nitro group of derivatives 9e11 in methanol with Pd/C under hydrogen atmosphere gave compounds 12e14 in good yields (73e82%).…”

“…In the first method, benzothiazolone 1 was brominated in CHCl 3 with Br 2 to afford the corresponding 6-bromobenzothiazolone 2 [27], with good yield (85%), which was allowed to react in DMF with potassium carbonate [28] and the corresponding 2-chloroethylalkylamine derivatives to yield the Nsubstituted compounds 3e4. The Stille reaction [29,30] was then performed in two steps to furnish final compounds.…”

Convenient synthesis and characterization of some novel benzothiazolone-based Schiff bases as potential pharmaceutically active agents

“…The identity of the known products 2(3H)-benzothiazolone derivatives 1, 2, 3a, 3b, 4a and 4b was confirmed by the comparison of their melting points and spectroscopic data with those of authentic compounds available in the literature. [35][36][37][38][39][40] General procedure for the preparation of nitro compounds (3a-3b):…”