Synthesis of 2,4-Diiodoquinolines via the Photochemical Cyclization of <i>o</i>-Alkynylaryl Isocyanides with Iodine

Mitamura, Takenori; Ogawa, Akira

doi:10.1021/jo1021772

Cited by 80 publications

(21 citation statements)

References 55 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…72 They performed the intramolecular cyclization of ortho-alkynylaryl isocyanides (41) with molecular iodine and UV radiation, with good yields and in considerably less time than most photocatalysed reactions.…”

Section: Scheme 11mentioning

confidence: 99%

Synthesis of Quinolines: A Green Perspective

Batista

Pinto

Silva

2016

ACS Sustainable Chem. Eng.

115

View full text Add to dashboard Cite

The quinoline scaffold is present in a vast number of natural compounds and pharmacologically active substances, comprising a significant segment of the pharmaceutical market. The classical methods for the synthesis of this heterocyclic skeleton require the use of expensive starting materials and high temperature conditions. Chemists play a fundamental role in the construction of a sustainable future through the pursuit of greener chemical processes. As so, the development of new synthetic methods using more efficient energy sources and less hazardous solvents as well as renewable and eco-friendly catalysts to attain the quinoline scaffold can provide significant environmental and economic advantages. This review unveils green methods used in the synthesis of quinolones. Important green metrics are calculated for each proposed method and the statistical analysis allowed us to propose the best approaches for further investigation. The applied research is eventually unveiling the full potential of Friedländer and/or multicomponent reactions, to improve atom economy. The quinoline structural motif is readily available through a number of classical synthetic routes and from commercially available reagents. The Friedländer synthetic method (A) from ortho-aminoacetophenones (10) and the Skraup (B), Combes (D) and Doebner-Miller (F) syntheses from anilines (11), as well as its adaptations, are good examples. Moreover, the Conrad-Limpach (C), Gould-Jacobs (E) and Camps (G) routes for the synthesis of quinolones are widely used methods (Scheme 1). Still, all classical methods have similar disadvantages, requiring highly acidic and/or oxidizing media, high temperatures and long reaction times.Moreover, most of these synthetic routes present selectivity problems with meta-substituted substrates and its versatility is limited by the reactivity of the methylenic carbon involved in the aldol reaction. 19 Although efficient and versatile, classical routes towards the synthesis of quinolines present serious environmental concerns as most synthetic routes use great excess of a reagents and produce a significant amount of toxic waste.

show abstract

Section: Scheme 11mentioning

confidence: 99%

Synthesis of Quinolines: A Green Perspective

Batista

Pinto

Silva

2016

ACS Sustainable Chem. Eng.

115

View full text Add to dashboard Cite

show abstract

“…The development of efficient method for their synthesis (113)(114)(115)(116)(117)(118)(119) or selective functionalization at different position is of immense importance (120)(121)(122)(123). Unlike C-2 position where the selectivity is based on inherent reactivity of the C=N or N-adjacent Alternative approach for the quinoline functionalization is installation of N-oxide in the quinoline moiety and its use as the DG.…”

Section: Sp2 C-h Activationmentioning

confidence: 99%

Distant C-H Activation/Functionalization: A New Horizon of Selectivity Beyond Proximity

et al. 2015

View full text Add to dashboard Cite

Activation/functionalization of inert C-H bond has undergone rapid growth in last decade and provides novel retro-synthetic disconnections for the synthesis of valuable molecules. The selectivity is often achieved by the use of directing group and is mainly limited to the proximal C-H bond. Initially, meta C-H activations were based on electronic or steric control and now it can be achieved by employing nitrile-based end-on-template as the directing group. The compilation of the remote C-H activation strategy will provide the useful linkage to the scientific community. This article is focused on recent progress in remote C-H activation, mechanistic understanding, and its applications in the field of total synthesis of targeted molecules.

show abstract

“…Recently, Mitamura et al [181] devised another expedient approach involving the intramolecular cyclization of oalkynylaryl isocyanides 286 to provide 2,4-diiodoquinolines 287 in moderate yields. In this process iodine serves as excellent catalyst in chloroform under photoirradiation conditions (Scheme 83).…”

Section: Synthesis Of Quinolines and Other Pyridine Condensed Compoundsmentioning

confidence: 99%

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

et al. 2015

View full text Add to dashboard Cite

One-pot heterocyclic synthesis is an exciting research area as it can open routes for the development of otherwise complex transformations in organic synthesis. Heterocyclic compounds show wide spectrum of applications in medicinal chemistry, chemical biology, and materials science. These heterocycles can be generated very efficiently through highly economical and viable routes using one-pot synthesis. In particular, the metal-free one-pot synthetic protocols are highly fascinating due to several advantages for the industrial production of heterocyclic frameworks. This comprehensive review is devoted to the transition metal-free one-pot synthesis of nitrogen-containing heterocycles from the period 2010-2013.

show abstract

Synthesis of 2,4-Diiodoquinolines via the Photochemical Cyclization of o-Alkynylaryl Isocyanides with Iodine

Cited by 80 publications

References 55 publications

Synthesis of Quinolines: A Green Perspective

Synthesis of Quinolines: A Green Perspective

Distant C-H Activation/Functionalization: A New Horizon of Selectivity Beyond Proximity

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

Contact Info

Product

Resources

About