Synthesis of New Aza Macrocyclic Diamides 2,2′‐Diaminodiphenyl Sulfide Using Crab‐Like Method

Abstract

Six new aza crown ethers (4–9) were synthesized based on the conventional route crab‐like method with the reaction of corresponding bis‐α‐chloroacetamidediphenylsulfide (BCADPS) (3) and aliphathic diamines (a–e) in refluxing acetonitrile in good yields. BCADPS (3) was synthesized with the reaction of 2,2′‐diaminodiphenyl sulfide (2) and chloroacetyl chloride. Interestingly, only the macrocyclization of BCADPS (3) with diamine (e) was led to the cryptand (9) in which methylene hydrogens were found as diastereotopic nucleis which is attributed to the rigidity of the cryptand (9). The formation of this cryptand (9) may be related the template effect of potassium ion. The structures of all compounds were confirmed using IR, 1H‐NMR, 13C‐NMR, mass spectroscopies, and elemental analysis.

Synthesis and Anticancer Evaluation of Some Novel Thiophene, Thieno[3,2‐d]pyrimidine, Thieno[3,2‐b]pyridine, and Thieno[3,2‐e][1,4]oxazepine Derivatives Containing Benzothiazole Moiety

“…It is worth mentioning that chloroacetyl chloride is commonly used with amino containing compounds to form chloroacetylamino derivatives that can react with thiocyanates followed by nucleophilic addition of imino moiety on carbonyl function of ester moiety at position 2. Thus, compound 14 reacted with chloroacetyl chloride to yield compound 15 , which underwent subsequent reaction with ammonium thiocyanate to afford the target compound 16 according to the proposed reaction mechanism (Fig.…”