40167-34-8

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 62, p. 2649, 1997 DOI: 10.1021/jo961981u

Upstream product

• 156469-70-4 (3R,4S)-4-Phenyl-pyrrolidine-3-carboxylic acid methyl ester 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 103-26-4 Methyl cinnamate 
• 103-26-4 methyl cinnamate 
• 170945-21-8 methyl 4-{[(trifluoromethyl)sulfonyl]oxy}-2,5-dihydrothiophene-3-carboxylate 
• 22097-90-1 2,5-dihydro-4-hydroxy-3-thiophenecarboxylic acid methyl ester 
• 5697-44-9 p-tolylsulfonylmethyl isocyanide 

Downstream Products

• 79205-17-7 methyl 5-(2',6'-dimethoxybenzoyl)-4-phenylpyrrole-3-carboxylate 
• 116267-86-8 3-Methyl-4-phenylpyrrole 
• 79600-73-0 methyl 4-phenyl-5-benzoylpyrrole-3-carboxylate 
• 56164-41-1 3-phenyl-pyrrole-2-carboxaldehyde 
• 881674-37-9 methyl 5-bromo-4-phenyl-1H-pyrrole-3-carboxylate 
• 79205-19-9 5-(2',6'-dimethoxybenzoyl)-4-phenylpyrrole-3-carboxylic acid 
• 79205-20-2 2-(2',6'-dimethoxybenzoyl)-3-phenylpyrrole 
• 79205-22-4 2-(2',6'-dihydroxybenzoyl)-3-phenylpyrrole 

Relevant academic research and scientific papers

Synthesis of Pyrroles via Consecutive 6π-Electrocyclization/Ring-Contraction of Sulfilimines

We present a modular, synthetic entry to polysubstituted pyrroles employing readily available 2,5-dihydrothiophenes. Ring-opening of the heterocycle provides access to a panel of 1,3-dienes which undergo pyrrole formation in the presence of inexpensive chloramine-T trihydrate. The transformation is conducted in an open flask and proceeds at ambient temperatures (23 °C) in nondry solvents. A careful adjustment of the electronics and sterics of the 1,3-diene precursor allows for the isolation of key intermediates. DFT studies identified a reaction mechanism that features a 6π-electrocyclization of a sulfilimine intermediate followed by spontaneous ring-contraction to reveal the pyrrole skeleton.

Mechanochemical Syntheses of N-Containing Heterocycles with TosMIC

A mechanochemical van Leusen pyrrole synthesis with a base leads to 3,4-disubstitued pyrroles in moderate to excellent yields. The developed protocol is compatible with a range of electron-withdrawing groups and can also be applied to the synthesis of oxazoles. Attempts to mechanochemically convert the resulting pyrroles into porphyrins proved to be difficult.

Metal-Free Directed C?H Borylation of Pyrroles

Robust strategies to enable the rapid construction of complex organoboronates in selective, practical, low-cost, and environmentally friendly modes remain conspicuously underdeveloped. Here, we develop a general strategy for the site-selective C?H borylation of pyrroles by using only BBr3 directed by pivaloyl groups, avoiding the use of any metal. The site-selectivity is generally dominated by chelation and electronic effects, thus forming diverse C2-borylated pyrroles against the steric effect. The formed products can readily engage in downstream transformations, enabling a step-economic process to access drugs such as Lipitor. DFT calculations (wB97X-D) demonstrate the preferred positional selectivity of this reaction.

Targeted Synthesis of Regioisomerically Pure Dodecasubstituted Type i Porphyrins through the Exploitation of Peri-interactions

A targeted synthesis of dodecasubstituted type I porphyrins that utilizes the reaction of unsymmetrical 3,4-difunctionalized pyrroles and sterically demanding aldehydes was developed. This way, type I porphyrins could be obtained as the only type isomers, likely due to a minimization of the steric strain arising from peri-interactions. Uniquely, this method does not depend on lengthy precursor syntheses, the separation of isomers, or impractical limitations of the scale. In addition, single-crystal X-ray analysis was used to elucidate the structural features of the macrocycles.

Polycyclic compound as well as pharmaceutical composition and application thereof

The invention discloses a polycyclic compound as well as a preparation method, a pharmaceutical composition and application thereof. The polycyclic compound (I), isomers, prodrugs, solvent compounds,hydrates, stable isotope derivatives or pharmaceutically

Symmetrical and Nonsymmetrical Meso-Meso Directly Linked Hydroporphyrin Dyads: Synthesis and Photochemical Properties

A series of a rigid meso-meso directly linked chlorin-chlorin, chlorin-bacteriochlorin, and bacteriochlorin-bacteriochlorin dyads, including free bases as well as Zn(II), Pd(II), and Cu(II) complexes, has been synthesized, and their absorption, emission, singlet oxygen (1O2) photosensitization, and electronic properties have been examined. Marked bathochromic shifts of the long-wavelength Qy absorption band and increase in fluorescence quantum yields in dyads, in comparison to the corresponding monomers, are observed. Nonsymmetrical dyads (except bacteriochlorin-bacteriochlorin) show two distinctive Qy bands, corresponding to the absorption of each dyad component. A nearly quantitative S1-S1 energy transfer between hydroporphyrins in dyads, leading to an almost exclusive emission of hydroporphyrin with a lower S1 energy, has been determined. Several symmetrical and all nonsymmetrical dyads exhibit a significant reduction in fluorescence quantum yields in solvents of high dielectric constants; this is attributed to the photoinduced electron transfer. The complexation of one macrocycle by Cu(II) or Pd(II) enhances intersystem crossing in the adjacent, free base dyad component, which is manifested by a significant reduction in fluorescence and increase in quantum yield of 1O2 photosensitization.

Beneficial Effects of Electrochemistry in Cross-Coupling Reactions: Electroreductive Synthesis of 4-Aryl- or 4-Heteroaryl-6-pyrrolylpyrimidines

The rarely described 4-(hetero)aryl-6-pyrrolylpyrimidines are prepared by electroreductive nickel-catalysed cross-coupling reactions between aryl halides and chloropyrimidines. Inherent predictable issues of such metal-catalysed reactions that involve or

Proton pump inhibitors

A proton pump inhibitor containing a compound represented by the formula (I) wherein X and Y are the same or different and each is a bond or a spacer having 1 to 20 carbon atoms in the main chain, R 1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, R 2 , R 3 and R 4 are the same or different and each is a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted thienyl group, an optionally substituted benzo[b]thienyl group, an optionally substituted furyl group, an optionally substituted pyridyl group, an optionally substituted pyrazolyl group, an optionally substituted pyrimidinyl group, an acyl group, a halogen atom, a cyano group or a nitro group, R 5 and R 6 are the same or different and each is a hydrogen atom or an optionally substituted hydrocarbon group, which has a superior proton pump action and shows an antiulcer activity and the like after conversion to a proton pump inhibitor in the body, or a salt thereof. or a prodrug thereof is provided.

Solvent-Controlled C2/C5-Regiodivergent Alkenylation of Pyrroles

A solvent-controlled C2/C5-selective alkenylation of 3,4-disubstituted pyrroles has been developed. The C3 substituent of pyrroles proved crucial to the regioselectivity. Substrates bearing directing groups at the C3 position exhibited excellent C2-select

Solvent-controlled switchable C-H alkenylation of 4-aryl-1H-pyrrole-3-carboxylates: Application to the total synthesis of (±)-rhazinilam

A solvent-controlled switchable C-H alkenylation of 4-aryl-1H-pyrrole-3-carboxylates via a Pd(OAc)2 catalyzed oxidative Heck reaction was first realized. The corresponding C2 and C5 alkenylation products were obtained in good yields with high regioselectivities, respectively. The selective C5-alkenylation was successfully applied to the total synthesis of (±)-rhazinilam.