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Authors = Shirley Muniz Machado Rodrigues

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10 pages, 2042 KiB  
Article
Practical Synthesis of 7-Bromo-4-chloro-1H-indazol-3-amine: An Important Intermediate to Lenacapavir
by Naeem Asad, Michael Lyons, Shirley Muniz Machado Rodrigues, Justina M. Burns, Thomas D. Roper, G. Michael Laidlaw, Saeed Ahmad, B. Frank Gupton, Douglas Klumpp and Limei Jin
Molecules 2024, 29(12), 2705; https://doi.org/10.3390/molecules29122705 - 7 Jun 2024
Cited by 2 | Viewed by 3069
Abstract
7-Bromo-4-chloro-1H-indazol-3-amine is a heterocyclic fragment used in the synthesis of Lenacapavir, a potent capsid inhibitor for the treatment of HIV-1 infections. In this manuscript, we describe a new approach to synthesizing 7-bromo-4-chloro-1H-indazol-3-amine from inexpensive 2,6-dichlorobenzonitrile. This synthetic method utilizes [...] Read more.
7-Bromo-4-chloro-1H-indazol-3-amine is a heterocyclic fragment used in the synthesis of Lenacapavir, a potent capsid inhibitor for the treatment of HIV-1 infections. In this manuscript, we describe a new approach to synthesizing 7-bromo-4-chloro-1H-indazol-3-amine from inexpensive 2,6-dichlorobenzonitrile. This synthetic method utilizes a two-step sequence including regioselective bromination and heterocycle formation with hydrazine to give the desired product in an overall isolated yield of 38–45%. The new protocol has been successfully demonstrated on hundred-gram scales without the need for column chromatography purification. This new synthesis provides a potential economical route to the large-scale production of this heterocyclic fragment of Lenacapavir. Full article
(This article belongs to the Special Issue Synthesis of Heterocyclic Compounds via Cycloadditions: Applications in Medicinal Chemistry)
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12 pages, 234 KiB  
Article
Side-chain Modifications of Highly Functionalized 3(2H)-Furanones
by Viviani Nardini, Shirley Muniz Machado Rodrigues, Maurício Gomes Constantino and Gil Valdo José da Silva
Molecules 2012, 17(10), 12151-12162; https://doi.org/10.3390/molecules171012151 - 16 Oct 2012
Cited by 6 | Viewed by 5019
Abstract
A series of 3(2H)-furanones, based on side-chain modifications of a parent 3(2H)-furanone, was synthesized in good yield. The parent compound was prepared by hydrogenolysis, and subsequent acid hydrolysis, of isoxazole derivatives. The isoxazole was prepared by a [3+2] 1,3-dipolar [...] Read more.
A series of 3(2H)-furanones, based on side-chain modifications of a parent 3(2H)-furanone, was synthesized in good yield. The parent compound was prepared by hydrogenolysis, and subsequent acid hydrolysis, of isoxazole derivatives. The isoxazole was prepared by a [3+2] 1,3-dipolar cycloaddition reaction between 3-butyn-2-ol and nitrile oxide. Full article
(This article belongs to the Section Organic Chemistry)
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