A Simple and Convenient Synthesis of Triprolidine

Rao, G. Venkateswara; Swamy, B. Narayana; Kumar, P. Hareesh; Reddy, G. Chandrasekara

doi:10.1080/00304940902802370

Cited by 6 publications

(3 citation statements)

References 8 publications

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“…The electron-donating methoxy group showed no change of benzoic acid reactivity, and 11d was isolated in 94% yield. A critical intermediate bearing a methyl group for the marketed allergy drug triprolidine, 11e , was readily isolated without chromatography in 75% yield. The desired ester ( 11f and g ) and nitrile ( 11h ) products from substituted benzoic acids were obtained in good to excellent yields with high functional group tolerance .…”

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confidence: 99%

A Nitrogen-Assisted One-Pot Heteroaryl Ketone Synthesis from Carboxylic Acids and Heteroaryl Halides

et al. 2016

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A practical and highly effective one-pot synthesis of versatile heteroaryl ketones directly from carboxylic acids and heteroaryl halides under mild conditions is reported. This method does not require derivatization of carboxylic acids (preparation of acid chlorides, Weinreb amides, etc.) or the use of any additives/catalysts. A wide substrate scope of carboxylic acids with high functional group tolerance has also been demonstrated. The results reveal that the presence of an α-nitrogen on the halide substrate greatly improves the desired ketone formation.

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confidence: 99%

A Nitrogen-Assisted One-Pot Heteroaryl Ketone Synthesis from Carboxylic Acids and Heteroaryl Halides

et al. 2016

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“…To demonstrate the synthetic application of this sequential photoredox protocol, we have accomplished the expedient synthesis of Triprolidine, a top-selling antihistamine that used for allergies 70,71 . As shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

Photoredox-catalyzed branch-selective pyridylation of alkenes for the expedient synthesis of Triprolidine

et al. 2019

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Alkenylpyridines are important pharmaceutical cores as well as versatile building blocks in organic synthesis. Heck reaction represents one of the most powerful platform for the construction of aryl-substituted alkenes, nevertheless, examples for Heck type coupling of alkenes with pyridines, particularly with branched selectivity, remain elusive. Here we report a catalytic, branch-selective pyridylation of alkenes via a sulfinate assisted photoredox catalysis. This reaction proceeds through a sequential radical addition/coupling/elimination, by utilizing readily available sodium sulfinates as reusable radical precursors as well as traceless elimination groups. This versatile protocol allows for the installation of important vinylpyridines with complete branched selectivity under mild conditions. Furthermore, this catalytic manifold is successfully applied to the expedient synthesis of Triprolidine.

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“…[104] Structurally belonging to the 1,1-diaryl-2-propyleneamine class of compounds, the synthesis of triprolidine (23.4) has been attempted by many research groups, representing a variety of approaches, with formation or functionalization of the characteristic CÀ C double bond being the most crucial and challenging part. Where construction of double bond has been attempted by either dehydration of the corresponding tertiary alcohol [105] or by the Wittig method, [106] its functionalization was suggested like many other aryl-substituted alkenes to occur via Heck reaction. [107] However, Heck coupling of alkenes with pyridines was found to be less feasible, owing to the potential coordination between the nitrogen atom and metal catalyst.…”

Section: Synthesis Of Triprolidinementioning

confidence: 99%

Growing Utilization of Radical Chemistry in the Synthesis of Pharmaceuticals

Gupta

Laha

2023

The Chemical Record

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Our current unhealthy lifestyle and the exponential surge in the population getting affected by a variety of diseases have made pharmaceuticals or drugs an imperative part of life, making the development of innovative strategies for drug discovery or the introduction of refined, cost‐effective and modern technologies for the synthesis of clinically used drugs, a need of the hour. Ever since their discovery, free radicals and radical cations or anions as reactive intermediates have captivated the chemists, resulting in an exceptional utilization of these moieties throughout the field of chemical synthesis, owing to their unprecedented and widespread reactivity. Sticking with the idea of not judging the book by its cover, despite the conventional thought process of radicals being unstable and difficult to control entities, scientists and academicians around the globe have done an appreciable amount of work utilizing both persistent as well as transient radicals for a variety of organic transformations, exemplifying them with the synthesis of significant biologically active pharmaceutical ingredients. This review truly accounts for the organic radical transformations including radical addition, radical cascade cyclization, radical/radical cross‐coupling, coupling with metal‐complexes and radical cations coupling with nucleophiles, that offers fascinating and unconventional approaches towards the construction of intricate structural frameworks of marketed APIs with high atom‐ and step‐economy; complementing the otherwise employed traditional methods. This tutorial review presents a comprehensive package of diverse methods utilized for radical generation, featuring their reactivity to form critical bonds in pharmaceutical total synthesis or in building key starting materials or intermediates of their synthetic journey, acknowledging their excellence, downsides and underlying mechanisms, which are otherwise poorly highlighted in the literature. Despite great achievements over the past few decades in this area, many challenges and obstacles are yet to be unraveled to shorten the distance between the academics and the industry, which are all discussed in summary and outlook.

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A Simple and Convenient Synthesis of Triprolidine

Cited by 6 publications

References 8 publications

A Nitrogen-Assisted One-Pot Heteroaryl Ketone Synthesis from Carboxylic Acids and Heteroaryl Halides

A Nitrogen-Assisted One-Pot Heteroaryl Ketone Synthesis from Carboxylic Acids and Heteroaryl Halides

Photoredox-catalyzed branch-selective pyridylation of alkenes for the expedient synthesis of Triprolidine

Growing Utilization of Radical Chemistry in the Synthesis of Pharmaceuticals

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