ChemInform Abstract: Anomalous Reaction of N‐Hydroxyalkyl‐N′‐Substituted Thioureas with Hexaethylphosphorous Triamide.

Mizrakh, L. I.; Polonskaya, L. Yu.; Gvozdetskii, A. N.; Berdyugin, V. V.; Vasil'ev, A. M.; Иванова, Т. М.

doi:10.1002/chin.198950073

Cited by 2 publications

(8 citation statements)

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“…The peaks M + 1 and M + 23 could easily be detected in most spectra. As described for similar compounds, 7f,11b the fragmentation patterns arise mainly from two decomposition routes (Scheme ). Path a takes place through a McLafferty-type fragmentation while route b involves the cleavage between the heterocyclic nitrogen and the (thio)carbonyl group.…”

Section: Resultsmentioning

confidence: 93%

“…It should be noted that structures with alkyl groups on both exocyclic nitrogen atoms (e.g., 14c , 14d ) fragment mainly following the pathway a , with M + 1 as the most abundant peak. The regioisomeric exo adducts, if present, would give a similar fragmentation pattern 7d 2 …”

Section: Resultsmentioning

confidence: 96%

“…Later, in 1928, German chemists reported that phenyl isothiocyanate adds to the endocyclic nitrogen of 2-amino-2-thiazoline ( 6 ) to form an adduct ( 7 ) which, upon heating, rearranges to the thioureido derivative 8 (Scheme ). Further reinvestigations of this research gave irreproducible and often contradictory results . 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 .…”

Section: Introductionmentioning

confidence: 99%

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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: Resultsmentioning

confidence: 93%

Section: Resultsmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

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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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“…N,N'-disubstituted hydrazine-1,2-carbothioamides 8a-c and substituted N',N'''-ethane-1,2-diylbis[N-substituted(thioureas)] 9a-c were prepared according to the literature procedures [31,[33][34][35][36][37].…”

Section: Methodsmentioning

confidence: 99%

“…It has been reported that ethylenediamine on reaction with allylisothiocyanate furnishes a linear thiourea, which in turn is cyclized to a bisthiazoline [31]. The present work was also undertaken to examine the reactions of 9a-c with 10a,b.…”

Section: Introductionmentioning

confidence: 95%

1,3,4-Thiadiazole, 1,3,4-thiadiazine, 1,3,6-thiadiazepane and quinoxaline derivatives from symmetrical hydrazine-1,2-dicarbothioamide as well as N, N″-ethane-1,2-diylbis(thiourea) derivatives

Hassan

Mourad

El‐Shaieb

et al. 2006

Journal of Heterocyclic Chemistry

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Reactions of N,N′‐disubstituted hydrazine‐1,2‐carbothioamides 8a‐c and substituted N,N″‐ethane‐1,2‐diylbis(thioureas) 9a‐c with 2,3,5,6‐tetrachloro‐1,4‐benzoquinone (chloranil, 10a) and 2,3,5,6‐tetrabromo‐1,4‐benzoquinone (bromanil, 10b) to form N,N′‐disubstituted 1,3,4‐thiadiazole‐2,5‐diamines 11a‐c, substituted 3‐amino‐6,7‐dichloro‐2,3‐dihydro‐1H‐4,2,1‐benzothiadiazine‐5,8‐diones 12a‐c, 2,3,7,8‐tetrahalothianthrene‐1,4,6,9‐tetrones 13a,b, substituted 5,6,8‐trihalo‐7‐oxo‐3,7‐dihydroquinoxaline‐2H‐carbothioamides 14a‐c, 15a‐c and 7‐substituted imino‐1,3,6‐thiadiazepane‐2‐thiones 16a‐c are reported.

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ChemInform Abstract: Anomalous Reaction of N‐Hydroxyalkyl‐N′‐Substituted Thioureas with Hexaethylphosphorous Triamide.

Cited by 2 publications

References 0 publications

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

1,3,4-Thiadiazole, 1,3,4-thiadiazine, 1,3,6-thiadiazepane and quinoxaline derivatives from symmetrical hydrazine-1,2-dicarbothioamide as well as N, N″-ethane-1,2-diylbis(thiourea) derivatives

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