Advances in direct C–H arylation of 5,5- 6,5- and 6,6-fused-heterocycles containing heteroatoms (N, O, S)

Kazzouli, Saı̈d El; Koubachi, Jamal; Brahmi, Nabil El; Guillaumet, Gérald

doi:10.1039/c4ra15384g

Cited by 87 publications

(38 citation statements)

References 163 publications

(94 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Based on the study by Chavez et al, the herein reported conditions in mesitylene appeared promising also for the copolymerization of 5‐BTz . However, neither the conditions of entries 1–5 nor variations involving co‐catalysts such as CuI, Cu(OAc) 2 or Ag salts did lead to coupling of NDIBr 2 and 5‐BTz (Table S1 supporting information) , …”

Section: Resultsmentioning

confidence: 77%

A Defect‐Free Naphthalene Diimide Bithiazole Copolymer via Regioselective Direct Arylation Polycondensation

et al. 2018

View full text Add to dashboard Cite

An optimized direct arylation polycondensation (DAP) protocol for the synthesis of a novel naphthalene diimide (NDI) 2,2′‐bithiazole (2‐BTz) copolymer (PNDI‐2‐BTz) is presented. The regioselective C–H activation of 2‐BTz at the 5‐positions allows for the synthesis of fully regioregular and homocoupling‐free PNDI‐2‐BTz of high molecular weight in less than 1 h in quantitative yield. Complete end group assignment shows functionalities according to monomer structures or to nucleophilic substitution, and allows for the reliable determination of absolute molecular weight. Compared to the well‐known bithiophene analog PNDIT2, an exceptionally high thermal stability, a hypsochromically shifted charge transfer absorption band and a lower‐lying LUMO energy level is found, making PNDI‐2‐BTz an interesting candidate for applications in organic electronic devices. In contrast to the selective and high yielding C–H activation of 2‐BTz at the 5‐position, the regioisomer 5,5′‐bithiazole is inactive under a variety of conditions.

show abstract

Section: Resultsmentioning

confidence: 77%

A Defect‐Free Naphthalene Diimide Bithiazole Copolymer via Regioselective Direct Arylation Polycondensation

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Accordingly, numerous synthetic methods for these scaffolds have been well established, including ring annulation and intermolecular cross-coupling. [19][20][21][22] Although a number of medicinal agents based on pyrrolo [1,2-a]pyrazine, another N-fused heterobicyclic system, have been disclosed in the literature, synthetic approaches to prepare this scaffold have been relatively underdeveloped, which prompted us to investigate the chemistry of pyrrolo [1,2-a]pyrazine. In this context, we have been involved in the design and synthesis of new chemical spaces based on the pyrrolo[1,2-a] pyrazine core (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Facile approach to benzo[d]imidazole-pyrrolo[1,2-a]pyrazine hybrid structures through double cyclodehydration and aromatization and their unique optical properties with blue emission

et al. 2020

View full text Add to dashboard Cite

A modular approach to polycyclic N-fused heteroaromatics is described. Acid-catalyzed reactions of various 1-(2-oxo-2-arylethyl)-1H-pyrrole-2-carbaldehydes with several o-phenylenediamines provided facile access to a number of new benzo[d]imidazole-pyrrolo[1,2-a]pyrazine hybrid structures through double cyclodehydration and aromatization. Optical characterization of the synthesized compounds revealed unique emission properties, with deep blue emission in the aggregated and solid states, and a dramatic substituent effect was observed. Fusion of an additional benzene ring into the benzo[4,5]imidazo[1,2-a]pyrrolo[2,1-c]pyrazine scaffold resulted in a remarkable increase in the intensity of blue fluorescence from the solution along with good cell permeability and negligible phototoxicity, indicating the potential for bioimaging applications. ; Fax: +82 2 884 8334; Tel: +82 2 880 2471 † Electronic supplementary information (ESI) available: 1 H and 13 C NMR spectra of synthesized compounds and CIF les for 8c. CCDC 1919367. For ESI and crystallographic data in CIF or other electronic format see

show abstract

“…5 Since that time, numerous studies on their synthesis, properties, and applications have been published, which have been partially collected in earlier reviews. Synthetic strategies leading to indolizines possessing additional exocyclic conjugated C-C double or triple bonds, as well as functionalization of the indolizine core 7 have been omitted here for the sake of brevity. The number of valuable contributions pressed us to be selective.…”

Section: Introductionmentioning

confidence: 99%

Recent advances in the synthesis of indolizines and their π-expanded analogues

2016

View full text Add to dashboard Cite

Indolizine (pyrrolo[1,2-a]pyridine) is one of the five isomers of indole and it serves as a precursor for widespread indolizidine alkaloids. The straightforward synthesis of indolizines based on classical methodologies such as Scholtz or Chichibabin reactions has overshadowed numerous new strategies that have been revealed especially within the last ten years. The desire to achieve substitution patterns which were hard to build sparked the discovery of completely new pathways, e.g. transition metal-catalyzed reactions and approaches based on oxidative coupling. In this review, selected strategies toward indolizines published since 2005 are briefly summarized, commented upon, compared, and illustrated. The literature discussed here involves reactions based on either pyridine or pyrrole scaffolds, as well as selected methodologies leading to π-expanded indolizines.

show abstract

Advances in direct C–H arylation of 5,5- 6,5- and 6,6-fused-heterocycles containing heteroatoms (N, O, S)

Abstract: This report aims to review the advances made in C–H arylation of 5,6, 6,6 and 5,5 fused-heterocyclic systems.

Cited by 87 publications

References 163 publications

A Defect‐Free Naphthalene Diimide Bithiazole Copolymer via Regioselective Direct Arylation Polycondensation

A Defect‐Free Naphthalene Diimide Bithiazole Copolymer via Regioselective Direct Arylation Polycondensation

Facile approach to benzo[d]imidazole-pyrrolo[1,2-a]pyrazine hybrid structures through double cyclodehydration and aromatization and their unique optical properties with blue emission

Recent advances in the synthesis of indolizines and their π-expanded analogues

Contact Info

Product

Resources

About