22118-93-0

Upstream product

• 3947-97-5 3-phenyl-3-cyclobutene-1,2-dione 
• 175225-79-3 3-chloro-2-hydroxy-4-phenyl-2-cyclobuten-1-one 
• 2892-63-9 3,4-Dichlorocyclobut-3-ene-1,2-dione 
• 71-43-2 benzene 
• 313-27-9 1-phenyl-3,3,4-trifluoro-4-chloro-1-cyclobutene 
• 313-28-0 3,3,4,4-Tetrafluor-1-phenyl-cyclobuten-⁽¹⁾ 
• 313-29-1 4-Fluor-4-chlor-1-phenyl-cyclobuten-⁽¹⁾-on-⁽³⁾ 
• 313-30-4 4,4-Difluoro-3-phenyl-cyclobuten-⁽²⁾-on-⁽¹⁾ 

Downstream Products

• 79033-48-0 N-(3,4-Dioxo-2-phenyl-1-cyclobuten-1-yl)-4-morpholincarboselenoamid 
• 76098-49-2 N-(3,4-Dioxo-2-phenyl-cyclobut-1-enyl)-pyrrolidine-1-carboximidoyl chloride 
• 78975-50-5 N-(3,4-Dioxo-2-phenyl-cyclobut-1-enyl)-pyrrolidine-1-carboximidoyl chloride 
• 76098-44-7 N-(3,4-Dioxo-2-phenyl-1-cyclobutenyl)-4-morpholincarboximidoylchlorid 
• 90234-77-8 N-(3,4-Dioxo-2-phenyl-1-cyclobuten-1-yl)-2-isoindolincarboximidoylchlorid 
• 76098-47-0 N-(3,4-Dioxo-2-phenyl-cyclobut-1-enyl)-aziridine-1-carboximidoyl chloride 
• 76098-45-8 C₁₉H₂₃ClN₂O₂ 
• 76098-46-9 C₁₇H₁₉ClN₂O₂ 
• 81144-14-1 (3,4-Dioxo-2-phenylcyclobut-1-enyl)(isopropyl)malonsaeure-dimethylester 
• 102266-26-2 N-(2,3-Dioxo-4-phenylcyclobutenyl)-S,S-dimethylschwefeldiimid 
• 81144-17-4 (3,4-Dioxo-2-phenylcyclobut-1-enyl)(phenyl)malonsaeure-dimethylester 
• 102266-28-4 S,S-Dibenzyl-N-(2,3-dioxo-4-phenylcyclobutenyl)schwefeldiimid 
• 76098-48-1 N-(3,4-Dioxo-2-phenyl-cyclobut-1-enyl)-azetidine-1-carboximidoyl chloride 
• 81144-16-3 (3,4-Dioxo-2-phenylcyclobut-1-enyl)(isopentyl)malonsaeure-dimethylester 

Relevant academic research and scientific papers

Synthesis and antitumor activity of novel 3,4-diaryl squaric acid analogs

A series of novel 3,4-diaryl squaric acid analogs 4a-r related to combretastatin A-4 (CA4) using squaric acid as the cis-restricted linker were prepared and studied for their anticancer activity against selected human cancer cell lines. New compounds 4g,

Synthesis of the substituted 3-cyclobutene-1,2-diones

A convenient synthesis of the novel squaric acid derivatives is reported. Unsymmetrically substituted 3,4-diamino-3-cyclobutene-1,2-diones and 3-amino-4-hydroxy-3-cyclobutene-1,2-diones were prepared by interaction of diethyl squarate with different nucle

Selective 1,4-addition of arenes to 3-chloro-3-cyclobutene-1,2-dione under friedel-crafts conditions. Synthesis and reactivity of 4-aryl-3-chloro-2- hydroxy-2-cyclobuten-1-ones

The reaction of semisquaric chloride (7) with arenes 2 has been investigated. In the presence of 1.1 equiv of AlCl3 and in the temperature range of -15° C to rt the arenes 2a-q afford the 4-aryl-3-chloro-2-hydroxy-2-cyclobuten-1-ones (chloroenols) 8a-q in good yield. By contrast, 7 reacts with 1,4-dimethoxybenzene (2l) in boiling CH 2Cl2 to give a mixture of (2,5-dimethoxyphenyl) cyclobutenedione (9a) (27% yield) and bis(2,5-dimethoxyphenyl)cyclobutenedione (10a) (8% yield). With 1,2,4-trimethoxybenzene (2r) in the presence of trifluoroacetic acid is generated (2,4,5-trimethoxyphenyl)-cyclobutenedione (9b) in 21% yield. The chloroenols 8 allow a series of valuable transformation reactions: with diazomethane the chloroenol methyl ethers 11 are generated, with chlorine the 3-aryl-4-chlorocyclobutenediones 12, and with bromine in MeOH the 3-aryl-4-methoxycyclobutenediones 13. In DMSO or in acetone/H2O the chloroenols 8 eliminate HCl, furnishing the arylcyclobutenediones 14. In a mixture of acetone-d6/D2O/DCl are obtained 4-aryl-cyclobutenediones-3-d 15. For the latter two processes the corresponding 3-aryl-4-chlorocyclobutane-1,2-diones 16 are postulated as intermediates. Thermolysis of the chloroenols 8 and the chloroenol methyl ethers 11 in refluxing m-xylene afforded the 3-chloro-1,2-dihydroxynaphthalenes 17 and the 3-chloro-1-hydroxy-2-methoxynaphthalenes 18, respectively.