Rongalite as C1 Synthon in the Synthesis of Divergent Pyridines and Quinolines

Gao, Huan; Zhou, Liyun; Wan, Jie‐Ping; Liu, Yunyun

doi:10.1021/acs.joc.3c00428

Cited by 19 publications

(7 citation statements)

References 74 publications

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“…The possibility of such cyclization is supported both by the isolation of the intermediate 5 and by the literature data. For example, enamines react with Rongalite and sulfonyl azide to give the pyridine derivatives and 1,2,3-triazoles, respectively. Besides this, there are also examples of the reactions of azomethynes, which involve a CN bond and result in pyrazolidin-3-one derivatives. , The next stage involves opening of the pyrrolidine ring with the formation of dihydropyridine I .…”

Section: Resultsmentioning

confidence: 99%

One-Step Synthesis of Functionalized Pyrazolo[3,4-b]pyridines via Ring Opening of the Pyrrolinium Ion

et al. 2023

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Herein, we report a highly regioselective one-pot synthesis of pyrazolo [3,4-b]pyridines via the reaction of 3-arylidene-1-pyrrolines with aminopyrazoles. The reaction proceeds through the sequential nucleophilic addition/electrophilic substitution/C−N bond cleavage and provides easy access to pyrazolo[3,4-b]pyridine derivatives featuring a primary amino group. Moreover, the reaction can be terminated at the electrophilic substitution stage, thus providing convenient entry to the hardly accessible pyrazolopyrrolopyridine scaffold.

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Section: Resultsmentioning

confidence: 99%

One-Step Synthesis of Functionalized Pyrazolo[3,4-b]pyridines via Ring Opening of the Pyrrolinium Ion

et al. 2023

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“…Quite recently, in 2023, Liu and co-workers have used rongalite as an inexpensive and proficient carbon synthon in the preparation of divergent pyridines (116 and 118) as well as quinolines 120 from enaminones/anilines or enaminones as the reaction partners (scheme 26). [47] Importantly, it has been noticed that as compare to the aldehydic synthons, the multifaced reagent rongalite displayed better yield of the products under operationally modest conditions. Interestingly, by using this protocol, they have not only synthesized the structurally symmetrical and unsymmetrical pyridines, but also prepared diverse quinoline derivatives.…”

Section: Synthesis Of Divergent Pyridines and Quinolinesmentioning

confidence: 99%

Recent Developments in Rongalite Chemistry: A Critical Review

Ali

2023

ChemistrySelect

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Rongalite whose chemical structure was discovered in 1905, is an inexpensive, easily assessable, and copious industrial product, which has significantly been used for a long time in rubber, dye, and veterinary industries. Moreover, it has also been used as an antidote against several heavy metals poisoning, in addition to its applications in the photographic developer and veterinary medicines. Gratifyingly, Rongalite has also shown its uses as the fungicidal, bactericidal and antioxidant in pharmaceutical formulation. Besides, it has also been used in material sciences, and also as a viable cosmetic hair‐dye‐color removers. Interestingly, in past decade, it has shown its high‐impact in the arena of synthetic organic chemistry serving as SO22− equivalent, C1 synthon donor, reducing agent/radical initiator or proton source ‐ to assemble diverse intricate organic molecules under operationally simple yet efficient conditions. However, the services of multiple features of Rongalite in synthetic chemistry are still at the research stage, and needs to be sophisticated to a higher level in many years to come. Considering the synthetic importance of this valued reagent, this review article presents the advancement made in the field of Rongalite chemistry in the past three years. This review article will update the researchers working in this arena about the advancement of Rongalite in the synthetic organic transformations as well as it will help readers wishing to deal with this easy‐to handle and eco‐friendly low‐cost commodity chemical. This review article updating the rongalite chemistry will be useful to the chemical community in general and synthetic chemists in particular.

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“…15 According to reported methodologies, rongalite can act as a reductant, proton source, 16 sulfonyl source 17 and C1 synthon in many synthetic organic transformations. 18–23 Rongalite is also employed as a C1 synthon in the construction of many heterocyclic compounds like furan, pyridine, quinoline 24 and chromones. 25 These examples underscore the extensive application scope of rongalite in emerging synthetic methodologies characterized by enhanced environmental sustainability.…”

Section: Introductionmentioning

confidence: 99%