ChemInform Abstract: Electronic Structure and Reactivity of 2‐Amino‐2‐thiazolin‐4‐one.

Рамш, С. М.; Храброва, Е. С.; Гинак, А. И.; Erusalimskii, G. B.

doi:10.1002/chin.198730188

ChemInform

1987

DOI: 10.1002/chin.198730188

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ChemInform Abstract: Electronic Structure and Reactivity of 2‐Amino‐2‐thiazolin‐4‐one.

С. М. Рамш¹,

Е. С. Храброва²,

А. И. Гинак³

et al.

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2006

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“…In the reactions of polydentate nucleophilic substrates (to which compound 1a can be assigned) with electrophilic reagents the central question is the regioselectivity of the process [7]. Through the aminomethylation of compound 1a using aqueous formaldehyde and secondary amines using the method proposed in [8] for the aminomethylation of pseudothiohydantoin with aqueous formaldehyde and piperidine, we have separated pure monoaminomethyl derivatives and the indicated question reduces to the structure of the compounds produced.…”

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2-Amino-5,5-bis(hydroxymethyl)-1,3-thiazol-4(5H)-one and its spirodioxane compounds in the Mannich reaction

Рамш¹,

Ivanenko²,

Medvedskiy³

et al. 2006

Chem Heterocycl Compd

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It was found that the aminomethylation of 2-amino-5,5-bis(hydroxymethyl)-1,3-thiazol-4(5H)-one and its spiro analogs using primary amines is accompanied by cyclization at the amidine fragment of the molecule with annelation of a tetrahydrotriazine ring. When using secondary amines the aminomethylation occurs at the exocyclic nitrogen atom.Keywords: 2-amino-5,5-bis(hydroxymethyl)-1,3-thiazol-4(5H)-one, 2-'amino-2-aryl(hetaryl)spiro-[1,3-dioxan-5,5'(4'H)-1',3'-thiazol]-4'-ones, 5-methyl-and 2-amino-5-ethyl-1,3-thiazol-4(5)-ones, aminomethylation.We have previously been able to prepare a 5,5-bis(hydroxymethyl) derivative of 2-amino-1,3-thiazol-4(5H)-one (pseudothiohydantoin) (1a) [1] and synthesize a series of spiro-[1,3-dioxan-5,5'(4'H)-1',3'-thiazole] derivatives (2a-e) from it [2]. Compound 1a is a "truncated" (fragmented) part of the compound 3a molecule which shows high biological activity [3]. This encouraged us to develop a novel method for the preparation of active compound 3a by the aminomethylation of the bis(hydroxymethyl) derivative 1a. This was particularly in view of the fact that the preparation of compound 3a, initially proposed via the direct aminomethylation of pseudothiohydantoin [3,4] is accompanied by the formation of a side reaction product and the yield of the target compound 3a does not exceed 30%. It also seemed suitable for developing a method of preparing homologs of compound 3a through the variation of the amino component in the aminomethylation reaction of compound 1a.With the aim of subsequently studying the biological activity of the newly obtained compounds and revealing a structure-activity relationship we have also synthesized in the work the monohydroxymethyl and spiro analogs of compound 3a using the 1b,c or spiro compounds 2a-e as substrates in the Mannich reaction and tert-butylamine or methylamine as the amino component. The aminomethylation of substrate 1a with secondary cyclic amines also gave the Mannich bases 5a,b, differing from compound 3a in the acyclic structure of the aminomethyl fragment of the molecule. Finally, the hydroxymethylation of the thiazolo[3,2-a]pyrimidine derivative 6 gave compound 7 as the "desaminated" analog of compounds 3a. __________________________________________________________________________________________

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2-Amino-5,5-bis(hydroxymethyl)-1,3-thiazol-4(5H)-one and its spirodioxane compounds in the Mannich reaction

Рамш¹,

Ivanenko²,

Medvedskiy³

et al. 2006

Chem Heterocycl Compd

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ChemInform Abstract: Electronic Structure and Reactivity of 2‐Amino‐2‐thiazolin‐4‐one.

Cited by 1 publication

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2-Amino-5,5-bis(hydroxymethyl)-1,3-thiazol-4(5H)-one and its spirodioxane compounds in the Mannich reaction

2-Amino-5,5-bis(hydroxymethyl)-1,3-thiazol-4(5H)-one and its spirodioxane compounds in the Mannich reaction

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