190273-04-2

Upstream product

• 190272-33-4 methyl 2-(2-methoxyphenyl)-1-tosyl-2,5-dihydro-1H-pyrrole-3-carboxylate 
• 135-02-4 ortho-anisaldehyde 
• 154243-37-5 2-[(2-Methoxy-phenyl)-(toluene-4-sulfonylamino)-methyl]-acrylic acid methyl ester 
• 23326-27-4 Methyl 2-butynoate 
• 100200-70-2 N-(2-methoxyphenyl)methylidene-4-methylbenzenesulfonamide 
• 18913-35-4 methyl buta-2,3-dienoate 
• 190272-84-5 2-(2-Methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrole-3-carboxylic acid methyl ester 

Downstream Products

• 69640-32-0 2-(2-methoxyphenyl)pyrrole 
• 10245-81-5 2,4-dibromo-6-(3,4,5-tribromo-1H-pyrrol-2-yl)phenol 
• 42041-50-9 2-(2-hydroxyphenyl)-1H-pyrrole 

Relevant academic research and scientific papers

Application of the ring-closing metathesis to the formation of 2-aryl-1H-pyrrole-3-carboxylates as building blocks for biologically active compounds

Ring-closing metathesis (RCM) is a powerful tool for the preparation of cyclic organic compounds. Yet, one of the major limitations of this method is the difficulty to prepare large quantities of target molecules. Herein we describe a comprehensive study

A Novel [3+2] Cycloaddition Approach to Nitrogen Heterocycles via Phosphine-Catalyzed Reactions of 2,3-Butadienoates or 2-Butynoates and Dimethyl Acetylenedicarboxylate with Imines: A Convenient Synthesis of Pentabromopseudilin

The reactivity of a new three carbon synthon, generated in situ from the reaction of 2,3-butadienoates 2-butynoates with an appropriate phosphine as the catalyst, toward the electron-deficient imines is described. Triphenylphosphine-catalyzed reaction of methyl 2,3-butadienoate with N-sulfonylimines gave the single [3+2] cycloadduct in excellent yield; tributylphosphine-catalyzed reaction of methyl 2,3-butadienoate or 2-butynoate with N-tosylimines afforded the corresponding [3+2] cycloadduct as the major product along with a small amount of the three components adduct. Aliphatic N-tosylimines gave moderate yield for this reaction. In addition, a new phosphine-catalyzed cyclization reaction of dimethyl acetylenedicarboxylate with N-tosylimines is also described. A reaction mechanism is proposed. Further elaborations of the cycloaddition products and the synthesis of pentabromopseudilin using this method are exemplified.

Phosphine-catalyzed [3+2] cycloaddition reaction of methyl 2,3-butadienoate and N-tosylimines. A novel approach to nitrogen heterocycles

In the presence of a catalytic amount of triphenylphosphine, methyl 2,3-butadienoate smoothly reacted with aromatic or heteroaromatic N-tosylimines at room temperature to afford the [3+2] cycloaddition product in excellent yield.