Reactions With Hydrazidoyl Halides. Ix: A Novel Synthesis of Some Hydrazidoyl Sulfides, Thiadiazolines,thiazoles and Coumarines

Reaction of thiocarboxanilide derivatives of 2-phenylimino-3-phenyl-4-thiazolidinone and 1,3-diphenyl-2-thioxo-4-imidazolone with hydrazonoyl halides and active chloromethylene compounds

“…analyses data of the products isolated are compatible with the two possible structures 7 and 10 (Scheme 1). However, the latter structure 10 was discarded as the reaction products were recovered unchanged after treatment with mercuric oxide in boiling acetic acid while the treatment is expected to convert 10 -if present-to 12, the C = S double bond is known to be more reactive dipolarophile than the C = C double bond [43], and reaction of acyclic β-ketothioanilides with 1 has been reported to give 2-alkylidene derivatives [44]. Accordingly, the product isolated from reaction 1a with 4A or 4B is assigned structure 7.…”

Hydrazonoyl halides: Useful building blocks for the synthesis of arylazoheterocycles

“…The reactions of N-aryl 2-oxopropanehydrazonoyl chlorides 2, 2-oxo-2-phenylethanehydrazonoyl bromides 5A [35] and N-aryl 2-heteroaryl-2-oxo-ethanehydrazonoyl bromides 6B,D,G [21,23,36] each with cyanothioacetamide were reported to give the respective 5-arylazo-4substituted thiazole derivatives 40 (Scheme 13). The latter products 40 were reported to couple with diazotized anilines to give 41 (Scheme 14) [23,35,36], and to condense with salicylaldehyde to afford 5-arylazo-2-(coumarin-3yl)-4-substituted thiazoles 42 (Scheme 14) [35,36].…”

Preparation of New Derivatives of Thiazole, Thiazolidine, and Thiazol-2-Ylpyrazolo[3,4-D]pyrimidine Sulfonamido Conjugates

“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] The thiazolidine moiety occurs in different bioactive substances as an important pharmacophoric group, for instance, the imidazo[2,1-b]thiazole system in the main moiety of the well-known antihelmintic and immunomodulatory agent levamisole. 16,17 Thiazol[2,3-a]pyrimidines bear a structure analogous to levamisol and have been well studied as immunomodulatory, anticancer, analgesic, and psychotropic agents.…”