New Knowledge of Thioammeline

Welcher, Richard P.; Kaiser, Donald W.; Wystrach, V. P.

doi:10.1021/ja01530a035

Cited by 12 publications

(6 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The 13 С NMR spectrum contained only two signals (160.4 and 181.9 ppm); this fact confirmed high-symmetric structure of the molecule. The IR spectrum of compound 12 was identical to that of thioammeline [27].…”

mentioning

confidence: 73%

“…The first synthesis of thioammeline 12 was performed via the reaction of ammonium thiocyanate with dicyanodiamide [26]. The procedure was then improved [27], and alternative synthetic routes involving dicyanodiamide and thiourea [28] or 2-chloro-1,3,5triazine-4,6-diamine and sodium thiosulfate [29] were developed. The identity of the prepared compound 12 and thioammeline was confirmed by a set of analytical data.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Some New Reactions and Properties of Xanthane Hydride (5-Amino-1,2,4-dithiazole-3-thione)

et al. 2018

View full text Add to dashboard Cite

Aminomethylation of xanthane hydride (5-amino-1,2,4-dithiazole-3-thione) with the RNH 2 -HCHO system has resulted in the formation of the derivatives of new heterocyclic system (3,7 ,3,5]triazine) in a low yield. The reaction of xanthane hydride with dicyandiamide has led to thioammeline [4,6-diamino-1,3,5-triazine-2(5Н)-thione]. Some practically important properties of xanthane hydride and its derivatives have been investigated. Xanthane hydride has efficiently exhibited carbon steel corrosion in neutral aqueous media. The prepared compounds have not exhibited growth-regulating or antidot activity superior to herbicide 2,4-D.

show abstract

mentioning

confidence: 73%

mentioning

confidence: 99%

Some New Reactions and Properties of Xanthane Hydride (5-Amino-1,2,4-dithiazole-3-thione)

et al. 2018

View full text Add to dashboard Cite

show abstract

“…58 Although a Mel-functionalized cyanohydrin was not formed in large amounts, the prebiotic formation of aminoalkyl nucleobases can also occur through nucleophilic aromatic substitution of sulfur-substituted heterocycles. 59,60 Thioammeline, which readily forms from the reaction of dicyandiamide (the dimer of cyanamide) with thiocyanate, 61 reacts with amines to form Mel derivatives. 62 The reaction of thioammeline with α-hydroxy-γ-aminobutyric acid (itself formed prebiotically from acrolein by the Cleaves−Miller path to γfunctionalized amino acids and hydroxy acids 53 ) gives the Melfunctionalized hydroxy acid, Mel HA (Figure 3C), in 13% yield, as estimated by 1 H NMR spectroscopy (see Section V of the SI).…”

Section: ■ Resultsmentioning

confidence: 99%

Depsipeptide Nucleic Acids: Prebiotic Formation, Oligomerization, and Self-Assembly of a New Proto-Nucleic Acid Candidate

et al. 2021

View full text Add to dashboard Cite

The mechanism by which informational polymers first formed on the early earth is currently unknown. The RNA world hypothesis implies that RNA oligomers were produced prebiotically, before the emergence of enzymes, but the demonstration of such a process remains challenging. Alternatively, RNA may have been preceded by an earlier ancestral polymer, or proto-RNA, that had a greater propensity for self-assembly than RNA, with the eventual transition to functionally superior RNA being the result of chemical or biological evolution. We report a new class of nucleic acid analog, depsipeptide nucleic acid (DepsiPNA), which displays several properties that are attractive as a candidate for proto-RNA. The monomers of depsipeptide nucleic acids can form under plausibly prebiotic conditions. These monomers oligomerize spontaneously when dried from aqueous solutions to form nucleobase-functionalized depsipeptides. Once formed, these DepsiPNA oligomers are capable of complementary self-assembly and are resistant to hydrolysis in the assembled state. These results suggest that the initial formation of primitive, self-assembling, informational polymers on the early earth may have been relatively facile if the constraints of an RNA-first scenario are relaxed.

show abstract

“…For these reasons, we report here the synthesis of 6-benzylthio-1,3,5-triazine-2,4-diamines through C–S bond formation using N -alkylpyridinium salts and NH 4 SCN as the starting materials. Compared with previous work, our method is superior as it is simple, efficient, and transition-metal-free. The use of cheap raw materials makes this method more practical.…”

Section: Introductionmentioning

confidence: 91%

Iodine-Mediated Heterocyclization for the Synthesis of 6-Alkylthio-1,3,5-triazine-2,4-diamines from N-Alkylpyridinium Salts and NH₄SCN

Liu,

Li,

Fan

et al. 2023

J. Org. Chem.

View full text Add to dashboard Cite

An iodine-mediated method for the synthesis of 6alkylthio-1,3,5-triazine-2,4-diamines by the reaction of N-alkylpyridinium salts and NH 4 SCN in air is reported. Twenty-seven compounds were obtained under the standard conditions. Pyridinium salts work as benzyl-group transfer reagents to promote the formation of the C Bn −S SCN bond and thereby the construction of the triazine skeleton. A plausible mechanism is proposed based on the experimental results and literature survey.

show abstract

New Knowledge of Thioammeline

Cited by 12 publications

References 1 publication

Some New Reactions and Properties of Xanthane Hydride (5-Amino-1,2,4-dithiazole-3-thione)

Some New Reactions and Properties of Xanthane Hydride (5-Amino-1,2,4-dithiazole-3-thione)

Depsipeptide Nucleic Acids: Prebiotic Formation, Oligomerization, and Self-Assembly of a New Proto-Nucleic Acid Candidate

Iodine-Mediated Heterocyclization for the Synthesis of 6-Alkylthio-1,3,5-triazine-2,4-diamines from N-Alkylpyridinium Salts and NH₄SCN

Contact Info

Product

Resources

About

New Knowledge of Thioammeline

Cited by 12 publications

References 1 publication

Some New Reactions and Properties of Xanthane Hydride (5-Amino-1,2,4-dithiazole-3-thione)

Some New Reactions and Properties of Xanthane Hydride (5-Amino-1,2,4-dithiazole-3-thione)

Depsipeptide Nucleic Acids: Prebiotic Formation, Oligomerization, and Self-Assembly of a New Proto-Nucleic Acid Candidate

Iodine-Mediated Heterocyclization for the Synthesis of 6-Alkylthio-1,3,5-triazine-2,4-diamines from N-Alkylpyridinium Salts and NH4SCN

Contact Info

Product

Resources

About

Iodine-Mediated Heterocyclization for the Synthesis of 6-Alkylthio-1,3,5-triazine-2,4-diamines from N-Alkylpyridinium Salts and NH₄SCN