3306-78-3

Upstream product

• 100-52-7 benzaldehyde 
• 3306-62-5 2-AMINOBENZENESULFONAMIDE 
• 103-82-2 phenylacetic acid 
• 100-51-6 benzyl alcohol 
• 108-88-3 toluene 
• 958-45-2 2-(benzylamino)benzenesulfonamide 
• 100-44-7 benzyl chloride 
• 5455-59-4 2-Nitrobenzenesulfonamide 
• 66081-21-8 2-azidobenzenesulphonamide 

Relevant academic research and scientific papers

Preparation method of benzothiadiazine-1, 1-dioxide compound

The invention relates to a synthesis method of a benzothiadiazine-1, 1-dioxide compound, and develops a novel solvent-free synthesis method of the benzothiadiazine-1, 1-dioxide compound. No solvent is added in the reaction process, and even part of the product can be obtained through separation without post-treatment. Therefore, the separation and purification process of the product is easy to implement, the reaction time is shortened, the yield of the product is increased, the yield can reach 73%-98%, the purity can reach 96%-99%, the use of toxic solvents is reduced to the greatest extent, and the problems of resource waste, environmental pollution and the like caused by the solvents are fundamentally solved. The method thoroughly eliminates the heavy metal pollution problem in the product from the source, is suitable for preparation of active pharmaceutical ingredients (API), biological agents and the like, and meets the requirements of green chemistry concept.

One-Pot, Borax-mediated synthesis of structurally diverse N, S-heterocycles in water

Herein, a borax–mediated convenient and efficient strategy for the synthesis of prominent structurally diverse N, S-heterocycles such as quinazolin-4(3H)-one, benzothiadiazine 1,1-dioxide, benzothioazole, and benzoxazoles from readily available 2-aminobenzamide/2-aminobenzenesulfonamide/2-aminothiophenol/2-aminophenol with α,α,α-trihalotoluenes at 100 ℃ in water is elaborated. Upon using aldehydes instead of α,α,α-trihalotoluenes, the reactions proceed through domino fashion under the catalytic effect borax to yield 2,3-dihydroquinazolin-4(1H)-one, 3,4-dihydrothiadiazine 1,1-dioxide, and benzothiazoles in one-pot at 60 ℃. The advantages of this protocol are practical simplicity, large substrate scope, moderate to excellent yields, and the use of water as the solvent.

Direct Use of Benzylic Alcohols for Multicomponent Synthesis of 2-Aryl Quinazolinones Utilizing the π-Benzylpalladium(II) System in Water

We demonstrate the direct use of benzylic alcohols for a multicomponent reaction of readily available isatoic anhydrides with amines in water, which is a synthetic route for the direct construction of a series of 2-aryl quinazolinones. This one-pot synthetic method involves the dehydrative N-benzylation of in situ generated anthranilamides followed by an amide-directed benzylic C?H amination process utilizing the π-benzylPd(II) system. Comparison of independent rate measurements using benzyl alcohol and its deuterated form gave a kinetic isotope effect of 3.5. Therefore, the benzylic C?H bond is cleaved in the rate-determining step. We successfully carried out a gram-scale reaction in 85% yield with simplified product isolation. (Figure presented.).

Synthesis of 2-aryl quinazolinones: Via iron-catalyzed cross-dehydrogenative coupling (CDC) between N-H and C-H bonds

Herein, we describe the direct synthesis of quinazolinones via cross-dehydrogenative coupling between methyl arenes and anthranilamides. The C-H functionalization of the benzylic sp3 carbon is achieved by di-t-butyl peroxide under air, and the subsequent amination-aerobic oxidation process completes the annulation process. Iron catalyzed the whole reaction process and various kinds of functional groups were tolerated under the reaction conditions, providing 31 examples of 2-aryl quinazolinones using methyl arene derivatives in yields of 57-95percent. The synthetic potential has been demonstrated by the additional synthesis of aryl-containing heterocycles. This journal is

Transition metal-catalyzed C–H functionalization of arylacetic acids for the synthesis of benzothiadiazine 1,1-dioxides

Copper-catalyzed practical route for the synthesis of benzothiadiazine 1,1-dioxides has been developed. The method involves C–H functionalization of arylacetic acids to form aromatic aldehydes and their subsequent condensation with 2-aminobenzenesulfonami

One-Pot Synthesis of Quinazolin-4(3H)-ones through Anodic Oxidation and the Related Mechanistic Studies

A metal-free and oxidant-free method for the one-pot preparation of quinazolin-4(3H)-ones enabled by electrochemical oxidation is described. Together with 2-aminobenzamides, a variety of aldehydes were successfully applied to an acid-catalyzed annulation and direct anodic oxidation cascade, affording structurally diverse quinazoline-4(3H)-ones in good to excellent yields. Additionally, certain alcohols can be directly applied instead of the corresponding aldehydes to achieve the same final products with the assistance of an electrolysis mediator (TEMPO). The reaction mechanism was carefully examined and the results strongly suggest that the direct and indirect oxidation go through different pathways. As an efficient and environmentally friendly access to a broad range of quinazolin-4(3H)-ones, the synthetic utility of this method was demonstrated by gram-scale operation, as well as the preparation of bioactive mackinazolinone and truncated erlotinib. (Figure presented.).

Metal-free oxidative synthesis of quinazolinones via dual amination of sp3 C-H bonds

A novel metal-free synthesis of quinazolinones via dual amination of sp3 C-H bonds was developed. The sp3 carbon in methylarenes or adjacent to a heteroatom in DMSO, DMF or DMA was used as the one carbon synthon. This journal is the Partner Organisations 2014.

Green approach toward one pot cascade synthesis of 3-aryl-3,4-dihydro-1,2,4 benzothiadiazine-1,1-dioxides

A silica-gel-supported ceric ammonium nitrate (CAN-SiO2) was found to be an effective catalyst for the cascade synthesis of functionalized 3-aryl-3,4-dihydro-1,2,4-benzo- thiadiazine-1,1-dioxides using 2-aminobenzenesulfonamide and benzaldehydes at room temperature. The reaction allows rapid cyclization (10-70 min) with 5 mol% CAN impregnated on silica gel to give the desired products in excellent yield without further column purification. The protocol uses inexpensive and environmentally friendly CAN-SiO2as the catalyst, and no ligand or additive was required. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental files: Additional figures]

Iron-catalyzed oxidative synthesis of N-heterocycles from primary alcohols

An iron-catalyzed one-pot one-step oxidative system has been successfully developed in the conversion of primary alcohols into nitrogen-containing heterocycles, such as quinazolinone, quinazoline and 3,4-dihydro-2H-1,2,4- benzothiadiazine 1,1-dioxide derivatives.

N-benzylation/benzylic C-H amidation cascade by the (ζ3- Benzyl)palladium system in aqueous media: An effective pathway for the direct construction of 3-phenyl-3,4-dihydro-(2H)-1,2,4-benzothiadiazine 1,1-dioxides

We demonstrate a unique strategy for a benzylation/benzylic C-H amidation cascade reaction by the (ζ3-benzyl)palladium system derived from a palladium catalyst and benzyl alcohol. This tandem process is devised as a new synthetic route for 3-phenyl-3,4-dihydro-(2H)-1,2,4-benzothiadiazine-1,1- dioxide. Water plays an important role for the smooth generation of the (ζ3-benzyl)palladium species, and a bis-benzylated Pd(II) intermediate would be formed in our catalytic system. Atom economical processes such as benzylic C-H activation, cascade reactions and chemoselective reactions in aqueous media have been developed.