Synthesis of tricyclic isoindoles and thiazolo[3,2-c][1,3]benzoxazines

Melo, Teresa M. V. D. Pinho e; Santos, Catarina I. A.; Gonsalves, Α. Μ. d’A. Rocha; Paixão, J. A.; Beja, Α. Matos

doi:10.1016/j.tet.2004.03.030

Cited by 15 publications

(6 citation statements)

References 18 publications

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“…The tridentate ligand 3b was synthesized by condensation of the cysteine methyl ester hydrochloride with salicylaldehyde. 38 In the alkylation of benzaldehyde with ZnEt 2 , this ligand led to moderate conversion and low ee, 10% ( Table 2, entry 2). This clearly demonstrates the negative effect of the presence of the hydroxyl group.…”

Section: Methodsmentioning

confidence: 99%

d-Penicillamine and l-cysteine derived thiazolidine catalysts: an efficient approach to both enantiomers of secondary alcohols

et al. 2016

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D-Penicillamine derived thiazolidine ligands were prepared in a two-step synthetic sequence and used in the enantioselective alkylation of a variety of aromatic aldehydes with diethylzinc at room temperature. Excellent ee, up to >99%, and nearly complete conversions were observed. Structurally analogous L-cysteine derived thiazolidine ligands were also synthesized and tested for comparative purposes, resulting in very good, albeit slightly lower selectivities, up to 89%. The combined use of these two types of thiazolidines constitutes a very interesting strategy for synthesizing both (S) and (R) enantiomers of chiral secondary alcohols, thus leading the way to a myriad of useful optically active products with opposite absolute configurations.

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Section: Methodsmentioning

confidence: 99%

d-Penicillamine and l-cysteine derived thiazolidine catalysts: an efficient approach to both enantiomers of secondary alcohols

et al. 2016

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“…The most interesting feature of these heterocycles is the possibility of carrying out diastereoselective reactions via a ring opening-ring closure mechanism. This chemical behavior has been explored for the synthesis of chiral thiazolidine-ring fused systems, as illustrated by the selective synthesis of thiazolo [2,3-b]isoindole derivative 2, 6,7 in which the creation of a new asymmetric centre is involved (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

ONE-POT DIASTEREOSELECTIVE SYNTHESIS OF CHIRAL TRICYCLIC l-CYSTEINE AND d-PENICILLAMINE DERIVATIVES: A LABORATORY EXPERIMENT

Soares¹,

Lopes²,

Murtinho³

et al. 2019

Quím. Nova

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Recebido em 10/07/2019; aceito em 22/08/2019; publicado na web em 21/11/2019 A one-pot diastereoselective synthesis of thiazolidine-ring fused systems derived from enantiomerically pure amino acids, l-cysteine or d-penicillamine, and achiral succindialdehyde is described as an experiment to be carried out by upper-division undergraduate students in a laboratory classroom. Reactions were performed under mild conditions, the products were isolated through simple experimental procedures and fully characterized. This study combines organic synthesis, determination of the purity of compounds (TLC analysis and melting point measurements), optical activity measurements as well as structural analysis (interpretation of 1D NMR and 2D NMR spectra). It offers a platform for the discussion of important organic chemistry concepts such as diastereoselectivity, kinetic control vs thermodynamic control and cyclization reactions via nucleophilic addition to imines/ iminium cations.

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“…36 Thiazolidine ligands were synthesized in three steps by condensation of (R)-Cys-OMe hydrochloride with benzaldehydes via 7a−j (Scheme 2). In contrast to the pyrrolidine route, this strategy allowed rapid access also to variations on the 2-position of the thiazolidine scaffold in a single step from readily available starting materials 38 and formation of the desired (2R,4R)-thiazolidine amide as the major product in the next step. 39 Condensation of (R)-Cys-OMe hydrochloride with aldehydes produced mixtures of C(2) epimeric methyl (4R)-2arylthiazolidine-4-carboxylates (7a−j).…”

Section: ■ Introductionmentioning

confidence: 99%

Discovery of a Potent Thiazolidine Free Fatty Acid Receptor 2 Agonist with Favorable Pharmacokinetic Properties

et al. 2018

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Free fatty acid receptor 2 (FFA2/GPR43) is a receptor for short-chain fatty acids reported to be involved in regulation of metabolism, appetite, fat accumulation, and inflammatory responses and is a potential target for treatment of various inflammatory and metabolic diseases. By bioisosteric replacement of the central pyrrolidine core of a previously disclosed FFA2 agonist with a synthetically more tractable thiazolidine, we were able to rapidly synthesize and screen analogues modified at both the 2- and 3-positions on the thiazolidine core. Herein, we report SAR exploration of thiazolidine FFA2 agonists and the identification of 31 (TUG-1375), a compound with significantly increased potency (7-fold in a cAMP assay) and reduced lipophilicity (50-fold reduced clogP) relative to the pyrrolidine lead structure. The compound has high solubility, high chemical, microsomal, and hepatocyte stability, and favorable pharmacokinetic properties and was confirmed to induce human neutrophil mobilization and to inhibit lipolysis in murine adipocytes.

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Synthesis of tricyclic isoindoles and thiazolo[3,2-c][1,3]benzoxazines

Abstract: Abstract-The thermolysis of (3R,9bS)-5-oxo-2, 3,5,9b-tetrahydrothiazolo[2,3-a]isoindole-3-carboxylic acids in Ac 2 O led to novel 3-methylene-2,5-dioxo-3H,9bH-oxazolo

Cited by 15 publications

References 18 publications

d-Penicillamine and l-cysteine derived thiazolidine catalysts: an efficient approach to both enantiomers of secondary alcohols

d-Penicillamine and l-cysteine derived thiazolidine catalysts: an efficient approach to both enantiomers of secondary alcohols

ONE-POT DIASTEREOSELECTIVE SYNTHESIS OF CHIRAL TRICYCLIC l-CYSTEINE AND d-PENICILLAMINE DERIVATIVES: A LABORATORY EXPERIMENT

Discovery of a Potent Thiazolidine Free Fatty Acid Receptor 2 Agonist with Favorable Pharmacokinetic Properties

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