40808-62-6

Upstream product

• 50551-29-6 2-pyrroleacetonitrile 
• 89532-48-9 Pyrrol-2-acetamid 
• 14745-84-7 2-(N,N-dimethylaminomethyl)pyrrole 
• 4778-25-0 (1H-pyrrol-2-yl)acetic acid ethyl ester 
• 276239-25-9 2-[(E)-2-nitroeth-1-enyl]-1H-pyrrole 
• 1003-29-8 2-pyrrole aldehyde 
• 72607-07-9 2-(2-nitrovinyl)pyrrole 
• 86688-93-9 1-benzenesulfonyl-2-formylpyrrole 

Downstream Products

• 855263-47-7 N-(2-pyrrol-2-yl-ethyl)-benzamide 
• 82859-02-7 4-carbethoxymethyl-4,5,6,7-tetrahydro<1H>pyrrolo<3,2-c>pyridine 
• 860362-26-1 4-methylpyrrolo[3,2-c]pyridine 
• 860721-07-9 4-phenyl-6,7-dihydro-1H-pyrrolo[3,2-c]pyridine 
• 942077-76-1 (2-pyrrolidin-1-ylethyl)carbamic acid tert-butyl ester 
• 1623752-27-1 benzyl (2-(1H-pyrrol-2-yl)ethyl)carbamate 

Relevant academic research and scientific papers

A Novel Sc(OTf)3-Catalyzed (2+2+1)-Cycloannulation/Aza-Friedel–Crafts Alkylation Sequence toward Multicyclic 2-Pyrrolines

The rapid assembly of molecular complexity continues to be at the forefront of novel reaction development. In the pursuit of that goal, we herein report a novel Sc(OTf)3-catalyzed, one-pot multicomponent reaction that furnishes complex multicyclic 2-pyrrolines with excellent overall yields and perfect diastereocontrol. This process is based on our previously established (2+2+1)-cycloannulation of in situ generated 1-azaallyl cations, 1,3-dicarbonyls and primary amines. The newly formed and highly reactive aminal moiety is readily substituted with indoles and pyrroles both as external and internal π-nucleophiles to provide densely functionalized N-heterocycles with four new σ-bonds and two vicinal quaternary stereogenic centers. In addition, DFT calculations have been conducted to further characterize the intermediate 1-azaallyl cations.

An Enantio- and Diastereoselective Mannich/Pictet–Spengler Sequence To Form Spiro[piperidine-pyridoindoles] and Application to Library Synthesis

A new tandem strategy based on a Mannich/Pictet–Spengler sequence has been developed and applied to the synthesis of a new small library (14 examples) of privileged compounds based on the spiro[piperidine-pyridoindole] core. The sequence proceeds by a diastereoselective Pictet–Spengler cyclization after condensation of several tryptamine derivatives with three novel piperidin-4-ones containing the fluorinated substituents F, CF3and SF5. The piperidin-4-ones were synthesized from readily available starting materials by an enantioselective multi-component organocatalytic Mannich reaction.

Rhodium enalcarbenoids: Direct synthesis of indoles by rhodium(II)- catalyzed [4+2] benzannulation of pyrroles

Disclosed herein is the design of an unprecedented electrophilic rhodium enalcarbenoid which results from rhodium(II)-catalyzed decomposition of a new class of enaldiazo compounds. The synthetic utility of these enalcarbenoids has been successfully demonstrated in the first transition-metal-catalyzed [4+2] benzannulation of pyrroles, thus leading to substituted indoles. The new benzannulation has been applied to the efficient synthesis of the natural product leiocarpone as well as a potent adipocyte fatty-acid binding protein inhibitor. Fat cat: A new class of enaldiazo compounds resulted in the first transition-metal-catalyzed [4+2] benzannulation of pyrroles to deliver indoles. The benzannulation is proposed to involve an unprecedented diacceptor rhodium enalcarbenoid. The reaction was used in the highly efficient synthesis of the natural product leiocarpone and a potent adipocyte fatty-acid binding protein inhibitor.