An efficient synthesis of dithiocarbamates under ultrasound irradiation in water

Abstract

Multicomponent reactions with ultrasonic activation have been used as a simple, rapid, atom economic, and green method for the synthesis of dithiocarbamate derivatives in water. The one-pot, three-component condensation of primary and secondary amines with carbon disulfide and unsaturated carbonyl compounds or alkyl halides under ultrasonic irradiation was developed as a green and fast protocol for the rapid high-yielding preparation of dithiocarbamates in water.

Ultrasound-Assisted Synthesis, Antifungal Activity against Fusarium oxysporum, and Three-Dimensional Quantitative Structure–Activity Relationship of N,S-Dialkyl Dithiocarbamates Derived from 2-Amino Acids

“…27 In the present study, we expand our search for promising antifungal agents, performing the derivatization of the conventional 2-amino acids l -alanine 2 , l -phenylalanine 3 , and l -tyrosine 4 (Figure 1) using a similar strategy to widen the available chemical space to access optimized antifungal action. Additionally, as a contribution to the green synthesis of these N , S -dialkyl dithiocarbamates, the present protocol also includes a previously reported ultrasound-assisted approach for other dithiocarbamate derivatives, 24 which importantly reduces the reaction time. Thus, this procedure can be considered attractive to synthesize these kinds of antifungal compounds since it is safer, nontoxic, cheaper, less time-consuming, and environment- and user-friendly.…”

Transition‐Metal‐Free C(sp3)–S Coupling in Water: Synthesis of Benzyl Dithiocarbamates Using Thiuram Disulfides as an Organosulfur Source

“…Thus, different bases were screened and K 2 CO 3 was chosen as the best one (entries [6][7][8]. As for benzyl bromides, substituents ranging from weak electron-withdrawing groups, such as Br and methyl ester, to strong electronwithdrawing groups, such as NO 2 , along with electron-donating methoxyl groups, all furnished the desired benzyl diethyldithiocarbamates in good yields (entries [15][16][17][18][19][20]. The optimal reaction conditions were summarized in entry 9 and the subsequent control experiments (entries [11][12] revealed that 100°C was the most suitable temperature for benzyl bromide.…”

“…Subsequently, substituted benzyl halides were treated with tetraethylthiuram disulfide (TETD) under the standard reaction conditions. As for benzyl bromides, substituents ranging from weak electron-withdrawing groups, such as Br and methyl ester, to strong electronwithdrawing groups, such as NO 2 , along with electron-donating methoxyl groups, all furnished the desired benzyl diethyldithiocarbamates in good yields (entries [15][16][17][18][19][20]. Due to the possible low reactivity of benzyl chloride, compounds 3u-3zb were obtained in moderate yields (entries 21-28).…”

“…Among these, several methods are available for the synthesis of benzyl dithiocarbamates in water, but they still have some drawbacks, such as long reaction time, and use of ultrasound irradiation that limit their utility and applicability. [18,19] Thus, more convenient and practical synthetic methods for these important compounds are still highly desirable. As part of our longstanding focus on developing dithiocarbamates [mostly on the C(sp 2 )-S bond formation] [20] and relevant applications, [21] as well as our efforts on organic reactions in water, [22] we hereby wish to report an efficient and practical method for the easy synthesis of benzyl dithiocarbamates by treating cheap and environmentally benign tetraalkylthiuram disulfides with substituted benzyl halides in water.…”

Progress in the Studies on Synthesis and Biological Properties of Dithiocarbamates

“…2012 年, Gholibeglo 等 [32] 利用超声的方法, 可在水 相快速地制备氨基二硫代甲酸酯类化合物. 与常规方法 相比, 超声促进的反应仅需 10 min 就能完成, 大大地缩 短了反应时间(Scheme 4).…”