[3+2]-cycloadditions of 1-Aza-2-azoniaallene cations to multiple bonds

Wang, Quanrui; Amer, Atef M.; Mohr, Susanne; Ertel, E.; Jochims, Johannes C.

doi:10.1016/s0040-4020(01)80194-0

Cited by 62 publications

(35 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Analogously, the heteroallene 7 carrying a tert-butyl group were used to synthesize neutral 2-substituted 1,2,4-triazoles [30,31]. Compounds 7, which formed at low temperature from 6 [15,18] and SbCl 5 , reacted with the isothiocyanate 9 via C S cycloaddition to give the nitrilium ion 13a as an intermediate.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of 3′‐1,2,4‐triazolo‐ and 3′‐1,3,4‐thiadiazoliminothymidines

Al‐Soud

Al‐Masoudi

2003

Heteroatom Chemistry

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

“…In situ deprotonation with aqueous NaHCO 3 [30,31] 33 were attributed to the methyl groups at C-5 of the triazole ring. The methyl and ethyl groups at N-1 were identified.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 3′‐1,2,4‐triazolo‐ and 3′‐1,3,4‐thiadiazoliminothymidines

Al‐Soud

Al‐Masoudi

2003

Heteroatom Chemistry

View full text Add to dashboard Cite

show abstract

“…Carbodiimides usually act as the two-electron component when reacting with 1,3-dipolar reagents such as 1-aza- 30 and 1,3-diaza-2-azoniallenes, 31 or with nitrile oxides and imines. 32 The 1:1 cycloaddition may be concerted or stepwise, and there is evidence for both pathways (Scheme 19).…”

Section: Mcrs By Cycloaddition On Carbodiimidesmentioning

confidence: 99%

Carbodiimides-Mediated Multi Component Synthesis of Biologically Relevant Structures

Bellucci¹,

Volonterio

2012

Organic Chemistry Insights

View full text Add to dashboard Cite

Multi-component reactions are very popular because they offer a wealth of products, while requiring only a minimum effort combining many elements of an ideal synthesis, such as operational simplicity, atom economy, bond-forming efficiency, and the access to molecular complexity from simple starting materials. As such, multi-component reactions have become the cornerstones of both combinatorial chemistry and diversity-oriented synthesis and thus playing a central role in the development of modern synthetic methodology for pharmaceutical and drug discovery research. In this Insight we will highlight the development of novel multi-component reactions based on the reactivity of carbodiimides, paying particular attention on their mechanistic features. We will address our attention on the process developed by us and others groups, in these last years, for the synthesis of biologically relevant structures such as, for example, heterocycles and glyco-conjugates.

show abstract

“…The synthesis of 3,4-dimethyl-3-pyridyl-4-yl-1-(2,4,6-trichlorophenyl)-3H- [1,2,4]-triazolium hexachloroantimonate from N-(1-pyridin-yl-ethylidene)-N H -(2,4,6-trichlorophenyl)-hydrazine (1d) and acetonitrile in the presence of a Lewis acid has been described previously [2]. The results of further experiments designed to explore the scope and the limitations of this procedure as a synthetic method for the formation of the pyridyl-triazolium salts 5a±b and 8d and the 3-pyridylindazoles 7 and 10e±g are the subject of the present investigation.…”

Section: Resultsmentioning

confidence: 99%

“…: 75 C; 1 Reactions of the -chloroarylazo compounds with propionitrile and formation of [1,2,4]triazolium hexachloroantimonates 5a±b and 9b…”

Section: -Chloro-1-pyridin-4-yl-ethyl-(246-trichlorophenyl)-diazenmentioning

confidence: 99%

Synthesis and Reactions of 1-Azo-2-azonia-allene Salts Derived from Pyridine Derivatives

Amer

1998

Monatshefte fuer Chemie

View full text Add to dashboard Cite

The 1-aza-2-azonia-allene salts prepared from 3-acetyl-or 3-benzoyl-pyridine via the corresponding hydrazone and -chloroaryl-azo derivatives react with propionitrile to afford the corresponding 3-(3-pyridyl)-1,2,4-triazolium salts. The intramolecular cyclization products could be only isolated as the main products if the intermediate -chlorophenyl-azo derivatives prepared from 4-benzoyl pyridine were treated with SbCl 5 in presence or absence of propionitrile. Also, only 3-methyl-1,2,3-triazolo[1,5-a]pyridinium salts were obtained by reaction of the cumulene prepared from 2-acetyl-pyridine with or without propionitrile in good yields. Treatment of 3-pyridylindazolium hexachloroantimonates and 3-methyl-1,2,3-triazolo[1,5-a]pyridinium salts with Na 2 CO 3 gave 3-pyridylindazoles and 3-methyl-1,2,3-triazolo[1,5-a]pyridine.

show abstract

[3+2]-cycloadditions of 1-Aza-2-azoniaallene cations to multiple bonds

Cited by 62 publications

References 51 publications

Synthesis of 3′‐1,2,4‐triazolo‐ and 3′‐1,3,4‐thiadiazoliminothymidines

Synthesis of 3′‐1,2,4‐triazolo‐ and 3′‐1,3,4‐thiadiazoliminothymidines

Carbodiimides-Mediated Multi Component Synthesis of Biologically Relevant Structures

Synthesis and Reactions of 1-Azo-2-azonia-allene Salts Derived from Pyridine Derivatives

Contact Info

Product

Resources

About