2-Imino-N-phenyl-3-thiazolidinecarboxamide, C10H11N3OS

Rasmussen, C. R.; Villani, Frank J.; Griffin, Edmund A.; Morrison, David S.; Olofson, R. A.

doi:10.1107/s0108270184010878

Cited by 3 publications

(1 citation statement)

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“…The selective attack at endocyclic or exocyclic nitrogen atoms of 6 as well as the structure of adducts, derived from phenyl isocyanate and phenyl isothiocyanate, were not clarified until 1986 when Rasmussen and co-workers pointed out the strict experimental conditions for rearrangement to occur . While the X-ray structure of 8 had previously been determined, these authors established the unequivocal structure of 9 by X-ray diffraction analysis . The results were interpreted by assuming that the kinetic control adducts 7 and 9 may undergo a facile intramolecular rearrangement, even at low temperatures and in the solid state (path a ), and/or dissociate to starting materials with further recombination at exocyclic nitrogen to yield the thermodynamically more stable products 8 and 10 (path b ).…”

Section: Introductionmentioning

confidence: 99%

Reactions of 2-Amino-2-thiazolines with Isocyanates and Isothiocyanates. Chemical and Computational Studies on the Regioselectivity, Adduct Rearrangement, and Mechanistic Pathways

Авалос¹,

Babiano²,

Cintas³

et al. 2000

J. Org. Chem.

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2-Amino-2-thiazoline derivatives bearing alkyl or aryl substituents at exocyclic nitrogen have been condensed with different isocyanates and isothiocyanates. The addition occurs at ring endocyclic nitrogen in a regiospecific manner to afford kinetic and enthalpy-favored adducts. The unequivocal assignment of these structures has been confirmed by X-ray diffraction analyses of several compounds. The endo adducts do not rearrange on heating with the sole exception of adducts in which the exocyclic nitrogen remains unsubstituted. Trapping experiments in the presence of other isocyanates or isothiocyanates produce the formation of new endo adducts by acyl exchange in the reaction mixture. Semiempirical PM3 calculations full corroborate the higher stability of endo or exo adducts depending on the substitution pattern. The formation of adducts is compatible with a stepwise reaction mechanism, for which semiempirical transition structures could be located in the potential energy surface, and the global energetics of the process have been determined. The formation of the endo adducts proceeds with a smaller activation barrier.

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Section: Introductionmentioning

confidence: 99%

Reactions of 2-Amino-2-thiazolines with Isocyanates and Isothiocyanates. Chemical and Computational Studies on the Regioselectivity, Adduct Rearrangement, and Mechanistic Pathways

Авалос¹,

Babiano²,

Cintas³

et al. 2000

J. Org. Chem.

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Comparative conformational analysis of two endothelin-B antagonists

et al. 1995

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A comparative conformational analysis of two short pseudopeptides with ETB receptor affinity has been performed by molecular modelling and NMR techniques. This analysis aimed to get insight into probable biorelevant conformations and pharmacophoric patterns necessary for an efficient interaction with the receptor. Thus, it was shown that the two compounds can adopt y-turn (or y-turn-like) conformations, based on which the synthesis of particular, more rigid analogs might be proposed. The results obtained should prove valuable in a strategy aiming to design new endothelin antagonists following a peptide to non-peptide approach.

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New investigation of the reaction of 2-amino-2-oxazolines with isocyanates and isothiocyanates. Evidence of a transposition during the second step

Bosc¹,

Jarry²,

Ouhabi³

et al. 1996

Can. J. Chem.

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The reaction of some 2-amino-2-oxazolines with isocyanates and arylisothiocyanates yields 3-monosubstituted or 2,3-disubstituted 2-iminooxazolidines depending on the experimental conditions and on the nature of the electrophile reactants. The structures of a mono- and a disubstituted derivative were established by X-ray analysis. The chemical behaviour of the compounds was investigated by molecular and quantum mechanics calculations. An intramolecular transposition during the second step of the reaction was found. Key words: 2-amino-2-oxazolines, iso(thio)cyanates, transposition. X-ray structure, MOPAC calculations.

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2-Imino-N-phenyl-3-thiazolidinecarboxamide, C10H11N3OS

Cited by 3 publications

References 1 publication

Reactions of 2-Amino-2-thiazolines with Isocyanates and Isothiocyanates. Chemical and Computational Studies on the Regioselectivity, Adduct Rearrangement, and Mechanistic Pathways

Reactions of 2-Amino-2-thiazolines with Isocyanates and Isothiocyanates. Chemical and Computational Studies on the Regioselectivity, Adduct Rearrangement, and Mechanistic Pathways

Comparative conformational analysis of two endothelin-B antagonists

New investigation of the reaction of 2-amino-2-oxazolines with isocyanates and isothiocyanates. Evidence of a transposition during the second step

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