Five‐Membered Heterocyclic Thiones. Part VII . 1,2,3‐ThiadiazoIe‐5‐thiolates

Demaree, Patricia; Doria, Marie-Carmen; Muchowski, Joseph M.

doi:10.1002/jhet.5570150811

Search citation statements

Order By: Relevance

Paper Sections

Select...

Wolff Synthesis1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

1979

2011

Publication Types

Select...

Article4

Other1

Relationship

Self Cite0

Independent5

Authors

Journals

Cited by 18 publications

(1 citation statement)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thus, 1,2,3-triazolo [4,5-b] [55], or by hydrolysis of the corresponding esters [56]. The acids can be easily converted by standard procedures into the corresponding esters, chlorides, amides, hydrazides, azides, thioamides, and nitriles [36,57].…”

Section: Wolff Synthesismentioning

confidence: 99%

Thiadiazoles

Chiacchio

Romeo

2011

Modern Heterocyclic Chemistry

View full text Add to dashboard Cite

Section: Wolff Synthesismentioning

confidence: 99%

Thiadiazoles

Chiacchio

Romeo

2011

Modern Heterocyclic Chemistry

View full text Add to dashboard Cite

ChemInform Abstract: FIVE‐MEMBERED HETEROCYCLIC THIONES. PART VII. 1,2,3‐THIADIAZOLE‐5‐THIOLATES

Demaree¹,

Doria²,

Muchowski³

1979

Chemischer Informationsdienst

View full text Add to dashboard Cite

show abstract

[2+3] Cycloadditions of ‘Thiocarbonyl Ylides’ (= (Alkylidenesulfonio)methanides) and diazoalkanes with N,N′‐(thiocarbonyl)diimidazole (= 1,1′‐(carbonothioyl)bis[1H‐imidazole])

Mlostoń¹,

Gendek²,

Linden³

et al. 1998

Helvetica Chimica Acta

View full text Add to dashboard Cite

Heating of a mixture of N,N′‐(thiocarbonyl)diimidazole (= 1,1′‐(carbonothioyl)bis[1H‐imidazole]; 1) and 2,5‐dihydro‐1,3,4‐thiadiazole 2a or 2b gave the 1,3‐dithiolanes 4a and 4b, respectively, via a regiospecific 1,3‐dipolar cycloaddition of the corresponding ‘thiocarbonyl methanides’ 3a,b onto the CS group of 1 (Schemes 1 and 2). The adamantane derivative 4b was not stable in the presence of 1H‐imidazole and during chromatographic workup. The isolated 1,3‐dithiole 5 is the product of a base‐catalyzed elimination of 1H‐imidazole from the initial cycloadduct 4b. The formation of the S,N‐acetal 6 can be rationalized by a protonation of the ‘thiocarbonyl ylide’ 3b followed by a nucleophilic addition of 1H‐imidazole. With the diazo compounds 8a–e (Scheme 3) 1 underwent a regiospecific 1,3‐dipolar cycloaddition to give the corresponding 2,5‐dihydro‐1,3,4‐thiadiazole derivatives 9, which spontaneously eliminated 1H‐imidazole to yield (1H‐imidazol‐1‐yl)‐1,3,4‐thiadiazoles 10. The structures of 10a and 10d were established by X‐ray crystallography. In the case of diazodiphenylmethane (8f), the initial cycloadduct 9f decomposed via a ‘twofold extrusion’ of N2 and S to give 1,1′‐(2,2‐diphenylethenylidene)bis[1H‐imidazole] (11; Scheme 3).

show abstract

Five‐Membered Heterocyclic Thiones. Part VII . 1,2,3‐ThiadiazoIe‐5‐thiolates

Abstract: The synthesis of the stable potassium salts of the first known 1,2,3‐thiadiazole‐5‐thiols is described.

Cited by 18 publications

References 8 publications

Thiadiazoles

Thiadiazoles

ChemInform Abstract: FIVE‐MEMBERED HETEROCYCLIC THIONES. PART VII. 1,2,3‐THIADIAZOLE‐5‐THIOLATES

[2+3] Cycloadditions of ‘Thiocarbonyl Ylides’ (= (Alkylidenesulfonio)methanides) and diazoalkanes with N,N′‐(thiocarbonyl)diimidazole (= 1,1′‐(carbonothioyl)bis[1H‐imidazole])

Contact Info

Product

Resources

About