147611-23-2

Upstream product

• 61495-07-6 N-(4-chloro-2-methylphenyl)benzamide 
• 98-88-4 benzoyl chloride 
• 95-69-2 4-chloro-2-methylbenzeneamine 
• 20028-53-9 2-amino-5-chlorobenzaldehyde 
• 591-50-4 iodobenzene 
• 4596-92-3 5-chloro-2,1-benzoisoxazole 
• 13939-06-5 molybdenum hexacarbonyl 
• 495-18-1 Benzohydroxamic acid 
• 587-04-2 m-Chlorobenzaldehyde 
• 19226-36-9 3-phenyl-5H-1,4,2-dioxazol-5-one 

Downstream Products

• 58058-53-0 6-chloro-2-phenylquinazoline 
• 1451360-05-6 (E)-6-chloro-2-phenyl-4-styrylquinazoline 
• 7033-51-4 6-chloro-2-phenyl-benzo[d][1,3]oxazin-4-one 

Relevant academic research and scientific papers

Experimental and computational studies on H2O-promoted, Rh-catalyzed transient-ligand-free ortho-C(sp2)-H amidation of benzaldehydes with dioxazolones

An efficient and convenient ligand-free, rhodium-catalyzed ortho-C(sp2)-H amidation of benzaldehydes with dioxazolones using H2O as the key promoter is described. Using this protocol, a wide range of benzaldehyde substrates were selectively amidated in good to excellent yields with broad functional group compatibility. KIE experiments revealed that the C-H bond activation was likely the rate-limiting step. In addition, computational studies indicated that the catalyst precursor interacted with water and dioxazolones to generate the active catalytic species. Notably, the practicality and efficacy of this method were illustrated by a late-stage amidation of an estrone-derived molecule and further transformations of the amidated product.

Pd/C-Catalyzed Aminocarbonylation of Aryl Iodides with Anthranils in Water Using Mo(CO)6 as the CO Source

A convenient procedure for the synthesis of N-(2-carbonylaryl)benzamides has been developed. Through Pd/C-catalyzed aminocarbonylation of anthranils with various hindered and functionalized aryl iodides, the desired amides were afforded in moderate to good yields. The protocol is advantageous due to the recyclable Pd/C catalyst, safe Mo(CO)6 as the solid CO source, and environmentally benign water as solvent. No inert atmosphere protection is needed.

TBHP/CoCl2-mediated intramolecular oxidative cyclization of N-(2-formylphenyl)amides: An approach to the construction of 4H-3,1-benzoxazin-4-ones

The intramolecular oxidative cyclization of N-(2-formylphenyl)amides has been realized through an oxidative C(sp2)-O(sp2) bond-forming reaction between an aldehyde carbon and amide oxygen. This new strategy, which uses tert-butyl hydroperoxide (TBHP) as an oxidant and CoCl2 as the catalyst, allows for the efficient Co-catalyzed synthesis of useful benzoxazin-4-one derivatives and features readily available starting materials and mild reaction conditions. The intramolecular cyclization of N-(2-formylphenyl)amides has been realized through an oxidative C(sp2)-O(sp2) bond-forming reaction between an aldehyde carbon and amide oxygen. This new strategy, which uses tert-butyl hydroperoxide (TBHP) as the oxidant and CoCl2 as the catalyst, allows for the efficient Co-catalyzed synthesis of useful benzoxazin-4-one derivatives.

KOtBu-mediated stereoselective addition of quinazolines to alkynes under mild conditions

A facile alkenylation of quinazolines with unactivated terminal alkynes has been achieved in the presence of KOtBu without the aid of any transition metal catalysts. The reaction is carried out under very mild conditions and shows a high stereoselectivity

Copper-catalyzed selective benzylic C-O cyclization of N-o-tolylbenzamides: Synthesis of 4 H-3,1-benzoxazines

A novel Selectfluor-mediated copper-catalyzed highly selective benzylic C-O cyclization for the synthesis 4H-3,1-benzoxazines is reported. The predominant selectivity for a benzylic C(sp3)-H over an aromatic C(sp 2)-H bond in N-o-tolylbenzamides is achieved.