New syntheses of thiadiazinones, thiazolidinedione hydrazones, and hydroxythiazoles from phenyl (trichloromethyl) carbinols

Reeve, Wilkins; Barron, Eugene

doi:10.1021/jo00901a010

Cited by 12 publications

(6 citation statements)

References 6 publications

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“…Estes compostos são muito importantes na química medicinal devido às suas atividades bioló-gicas, tais como antimicrobiana 57 , antiprotozoária 70 , fungicida 71 , antituberculose 72 , entre outras. As 4-tiazolidinonas podem ser sintetizadas a partir de tiossemicarbazonas como demonstraram Reeve e Barron 73 . Nesse trabalho, as tiazolidinonas foram obtidas da reação entre tiossemicarbazonas e fenil (triclorometil) carbinol, como único produto reacional, com rendimentos variando entre 31 a 79% (Esquema 8, Equação 2).…”

Section: Obtenção De 4-tiazolidinonasunclassified

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Tiossemicarbazonas: métodos de obtenção, aplicações sintéticas e importância biológica

Tenório¹,

Góes²,

Lima³

et al. 2005

Quím. Nova

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Section: Obtenção De 4-tiazolidinonasunclassified

“…Isto levaria à formação de um intermediário cloreto de áci-do que, finalmente, ciclizaria para formar a tiazolidinona 73 . Outra forma de obter 4-tiazolidinonas substituídas na posição 5, a partir de tiossemicarbazonas, é através da reação destas com anidrido maléico 69,74 (Esquema 8, Equação 3).…”

Section: Obtenção De 4-tiazolidinonasunclassified

Tiossemicarbazonas: métodos de obtenção, aplicações sintéticas e importância biológica

Tenório¹,

Góes²,

Lima³

et al. 2005

Quím. Nova

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“…The 2,2-dichloro-3-phenyloxirane 93 was formed by reaction of 2,2,2-trichloro-1-phenylethanol 92 with ethylene glycol (Scheme 22). [100] In case of thiosemicarbazide reaction with DMAD, many earlier research articles reported conflicting results about the produced intermediates 95-98 from the same reaction (Scheme 23). [101,102] The assignment of products in these reports depended on available preliminary analytical methods by hydrolyzing the products and recognizing the hydrolyzed substances, then predicting of the essential product.…”

Section: From Thiosemicarbazide/thiosemicarbazonementioning

confidence: 99%

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

et al. 2023

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Thiazolidinedione (TZD) is one of the privileged heterocyclic rings and has shown many biological applications in medicinal chemistry and drug discovery. This review covers the synthetic approaches of TZD and its derivatives, different synthetic techniques for affording the desired regioselectivity and stereoselectivity, and the techniques that would enhance reaction conditions such as microwave, one‐pot, or ultrasound synthesis. It focuses on synthetic challenges of glitazones and the transformation of other heterocycles to TZD. Moreover, the chemical and biological behavior of TZD through the substitution in the N3 position, modification of the C5 position, annealing in complex heterocyclic systems, and hybridization with other pharmacologically attractive moieties are discussed. All reactions mentioned are provided as possible with different reaction conditions, mechanisms, derivatives scope, yield and clarified by applications of such reactions in the construction of potential medicinal agents. The review also answers questions about rapid racemization of glitazones, their toxicity, considering TZD as pan‐assay interference compounds (PAINS) or not, and the influence of saturation of 5‐position of TZD in their biological activities. This review is a comprehensive guide to make informed decisions for construction of TZD derivatives with biological potentials.

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“…As shown in Fig. 3, our conceived carbinol would undergo conversion into the corresponding gem-dihaloepoxide which, upon attack of the phenoxide nucleophile, would provide the corresponding acyl halide, immediately converted in the reaction medium into the desired carboxylic acid [18][19][20][21].…”

mentioning

confidence: 98%

A Jocic-type approach for a practical and scalable synthesis of pyrrolonaphthoxazepine (PNOX)-based potent proapoptotic agents

Federico

Khan

Relitti

et al. 2018

Tetrahedron Letters

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We developed a Jocic-type protocol for the construction of the pyrrolonaphthoxazepine (PNOX) core. After an initial investigation based on the isolation of a trichloromethyl carbinol derivative, we shifted our attention towards a multicomponent single-step protocol. Screening of a variety of bases and solvents led to the identification of the optimum conditions for the preparation of the key a-aryloxy carboxylic acids to undergo intramolecular cyclization. The novel chemical route significantly improved overall yields for the preparation of PNOX-based compounds and was successfully extended to the preparation of 1,4-benzoxazinone-based templates.

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New syntheses of thiadiazinones, thiazolidinedione hydrazones, and hydroxythiazoles from phenyl (trichloromethyl) carbinols

Cited by 12 publications

References 6 publications

Tiossemicarbazonas: métodos de obtenção, aplicações sintéticas e importância biológica

Tiossemicarbazonas: métodos de obtenção, aplicações sintéticas e importância biológica

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

A Jocic-type approach for a practical and scalable synthesis of pyrrolonaphthoxazepine (PNOX)-based potent proapoptotic agents

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