No abstract

The acetylindolinyl sulfonamides (III) are prepared by reacting the sulfonyl chlorides (I) with the amino acid derivatives (II).

Twenty‐two derivatives of type (III), (V), (VI) and (VIII) are synthesized.

Reaction of 2-(quinolin-8-yloxy)acetohydrazide 1with phenyl isothiocyanate, carbon dsulphide, nitrous acid,active methylene compound and aromastic aldehydes afforded different heterocyclic compounds containing quinoline moiety 2-11. The structures of the new compounds confirmed by elemental analyses,spectroscopic measurements and chemical reactions.

Thiophene-2-carboxanilide and its p-chlora and p-bromo derivatives react with chlorosulfonic acid toMany heterocyclic compounds have been developed as commercial pesticides [1]. At the same time several sulfonyl derivatives such as amides, azides, and hydrazides have shown valuable biological activity [2-9] as, for example, antibacterials, fungicides, and nematicides. As a part of our research on the synthesis of novel pesticides, it therefore seemed useful to examine the biological properties of a series of heterocyclic sulfonyl derivatives. This idea was supported by the reported fungicidal activity exhibited by certain heterocyclic sulfonamides. I X = CI; z-t5 X = R (cf . Table 1) In the present work we examined the reaction of thiophene-2-carboxanilide as well as ofp-chloro-and p-bromoanilides with chlorosulfonic acid.Thiophene-2-carboxanilide reacts with excess chlorosulfonic acid (6 mol) at 40~ to give an excellent yield (80%) of the 4'-sulfonyl chloride 1 as the sole product. The interaction of the same reagents at higher temperature causes C-N bond cleavage to give thiophene-2-carboxylic acid. The orientation of sulfonation is presumably a reflection of the deactivating influence of the 2-carbamoyl group on the thiophene ring, making the phenyl ring the preferred site for electrophilic substitution. Sulfonyl chloride 1 was reacted with some amino acids and gave the respective N-sulfonylamino acids 2-6. The acids 2, 4, and 5 were converted successively to methyl esters 7-9 and hydrazides 10-12 or dipeptide derivatives 13-15. The structures of some of the derivatives 2-15 were supported by the PMR spectra, which clearly showed the pattern for the resonances of the aromatic protons. The m/z values and fragmentation data for compound 3 are also in accordance with its structure.The IR spectra of thiophene-2-carboxanilide derivatives showed sharp absorption bands in the 3120-2900 era-1 region which are associated with the thiophene C-H stretching vibrations. The sulfonyl group showed two characteristic bands in the regions 1380-1320 and 1180-1165 cm -1 while those compounds with amino group of amino acids showed the normal N-H stretching vibrations [10].