232262-80-5

Upstream product

• 2512-27-8 4-phenyl-piperazine-1-carbothioic acid phenylamide 
• 1224507-81-6 C₁₇H₁₈IN₃S 
• 92-54-6 4-phenyl-1-piperazine 
• 98041-44-2 2-iodophenyl isothiocyanate 
• 103-72-0 phenyl isothiocyanate 
• 1513865-35-4 (1H-benzo[d][1,2,3]triazol-1-yl)(4-phenylpiperazin-1-yl)methanethione 
• 95-16-9 1,3-Benzothiazole 
• 149-30-4 2-Mercaptobenzothiazole 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 

Relevant academic research and scientific papers

Electrochemical intramolecular dehydrogenative C-S bond formation for the synthesis of benzothiazoles

An external oxidant-free intramolecular dehydrogenative C-S cross-coupling has been developed under undivided electrolytic conditions. Various 2-aminobenzothiazoles could be synthesized with up to 99% yield from the direct combination of aryl isothiocyanates with amines. In the presence of a base, this reaction protocol is also applicable for the synthesis of benzothiazoles from N-aryl thioamides.

Copper(ii) ions supported on functionalized graphene oxide: an organometallic nanocatalyst for oxidative amination of azolesviaC-H/C-N bond activation

Graphene oxide (GO) was chemically modified withpara-aminobenzoic acid (PABA) to immobilize copper(ii) ions on its surface and used as a nanocatalyst for the oxidative C(sp2)-H bond amination reaction. A practical method to prepare Cu2+supported onpara-aminobenzoic acid grafted on GO was reported. The prepared Cu2+@GO/PABA was characterized by FT-IR, XRD, SEM, AFM, TEM, UV-Vis, and ICP techniques. The results showed that the morphology, distribution, and loading of copper ions could be well-adjusted by grafting of PABA on GO. Moreover, just 2 mol% of Cu2+@GO-PABA could catalyze the C-H activation reaction of benzoxazole and benzothiazole with secondary amines in >94% yields. Also, the catalyst showed very good recyclability and much less leaching of the Cu into the reaction solution. The high activity of Cu2+@GO-PABA can be ascribed to the good synergistic effects of Cu2+andpara-aminobenzoic acid grafted on graphene oxide.

Dioxygen-triggered oxidative cleavage of the C-S bond towards C-N bond formation

Research on the cleavage of C-C bonds has been well developed. By comparison with this, the activation of C-S bonds remains challenging. Herein, dioxygen-triggered oxidative cleavage of C-S bonds has been achieved, delivering a series of N-containing heterocyclic compounds that are frequently found in pesticides and pharmaceuticals. Additionally, the potential utility of this protocol was further demonstrated by a gram-scale experiment. Mechanistically, dioxygen plays a key role in the cleavage of C-S bonds towards C-N bond formation.

Metal free amination of 2-chloroazoles in aqueous medium

A green approach for the synthesis of 2-amino azoles by the reaction of 2-chloro azoles with various types of amines using water as an environment friendly solvent at room temperature has been developed. The significant features of this methodology are short reaction time and easy product separation. This approach provides various biologically active compounds in good to excellent yields without adding any catalyst, ligand, or base.

Synthesis of 2- N / S / C -substituted benzothiazoles via intramolecular cyclative cleavage of benzotriazole ring

The synthesis of numerous 2-N/S/C-substituted benzothiazoles was achieved from substituted thiocarbonylbenzotriazoles via free-radical intramolecular cyclative cleavage of the benzotriazole ring in the presence of (TMS) 3SiH and AIBN under mild

Ru/C: A simple heterogeneous catalyst for the amination of azoles under ligand free conditions

A ligand free Ru/C-catalyzed amination of 2-halo azoles with a broad scope of aminating reagents has been developed. A variety of 2-aminoazole derivatives were synthesized in moderate to good yields by utilizing this protocol. The methodology is operationally simple and not sensitive to air and moisture. It provides potentially useful products by using an inexpensive and recyclable catalytic system under ligand free conditions without significant loss of its catalytic activity up to four cycles. This journal is

A ligand free copper(II) catalyst is as effective as a ligand assisted Pd(II) catalyst towards intramolecular C-S bond formation via C-H functionalization

Copper(I) catalysts are usually ineffective on the other hand Pd(II) catalysts are quite effective in promoting intramolecular sp2 C-H functionalization (C-S bond formation). Herein, we have developed a ligand assisted Pd(II) catalyzed C-S bond formation via C-H activation from arylthioureas leading to the formation of 2-aminobenzothiazoles for substrates bearing electron donating (EDG) groups in the aryl ring. However without the assistance of ligand this Pd(II) catalyzed reaction is quite unproductive particularly for thioureas possessing strongly electron donating groups in the aryl rings. Interestingly, the ligand free Cu(II) catalyzed oxidative cyclization of arylthioureas are equally effective both for arylthioureas possessing electron donating as well as electron withdrawing groups in the aryl rings.

An "on-water" exploration of CuO nanoparticle catalysed synthesis of 2-aminobenzothiazoles

An "on-water" one-pot process has been engineered for the preparation of 2-aminobenzothiazole from ortho-halo (-F, -Cl, -Br and -I) substituted unsymmetrical thioureas. For ortho -I and -Br substrates the reactions afford 2-aminobenzothiazoles under metal free condition promoted by base. However, the relatively inert ortho -Cl and -F substrates undergo intramolecular arylthiolation only in the presence of CuO nanoparticles yielding 2-aminobenzothiazoles. This methodology provides easy access to aminobenzothiazoles utilising even the ortho -Cl and -F substrates. The catalyst is recyclable several times without loss of substantial activity. Other remarkable features include the wide range of functional group tolerance, absence of chromatographic purification (for ortho -I and -Br substrates) and providing moderate to excellent yield of the products under mild conditions, thus rendering the methodology as a highly eco-friendly alternative to the existing methods.

Metal-free synthesis of 2-substituted (N, O, C) Benzothiazoles via an intramolecular C-S bond formation

An efficient, economical, and convenient method was developed for the preparation of 2-substituted (N, O, C) benzothiazoles from N′-substituted- N-(2-halophenyl)thioureas, O′-substituted-N-(2-halophenyl) carbamothioates, or N-(2-halophenyl) thioamides via a base-promoted cyclization in dioxane without any transition metal. A one-pot variant combining the synthesis of the thiourea and the cyclization was also demonstrated. High yields were obtained, and a variety of functional groups were tolerated under these conditions. Transition-metal-free, mild reactive conditions, wide application scope, and shorter reaction times make this method superior to the reported methods for the synthesis of 2-substituted benzothiazoles and suitable for combinatorial format.

Heterocycle formation via palladium-catalyzed intramolecular oxidative C-H bond functionalization: An efficient strategy for the synthesis of 2-aminobenzothiazoles

N-Arylthioureas are converted to 2-aminobenzothiazoles via Intramolecular C-S bond formation/C-H functionalization utilizing an unusual cocatalytic Pd(PPh3)4MnO2 system under an oxygen atmosphere at 80 °C. This method elim