Triazoles. Part III. Mono- and di-methyl(phenyl)-1 : 2 : 4-triazoles

Atkinson, M. R.; Polya, J. B.

doi:10.1039/jr9540003319

Cited by 46 publications

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“…As an example, N-tosylamidrazones 160 can react either with acid chlorides or with ethyl chloroformate to give tosylated 1,2,4-triazoles 161 or 1,2,4-triazole-3-ones 162, respectively (Scheme 12.52) [212]. Other amidrazone reactions can occur with carboxylic acids [213], cyanogen bromide [214], aldehydes [215], and orthoesters [215,216]. Amidrazones 163 have been oxidized to 1,3,5-trisubstituted 1,2,4-triazoles 164 in good yields by silver carbonate, Dess-Martin periodinane, sodium and calcium hypochlorites, and tetrapropylammonium perruthenate (TPAP)/N-methylmorpholine N-oxide (NMO) combination (Scheme 12.53) [217][218][219].…”

Section: Reactions Of Hydrazonesmentioning

confidence: 98%

Five‐Membered Heterocycles with Three Heteroatoms: Triazoles

Yet

2011

Modern Heterocyclic Chemistry

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Section: Reactions Of Hydrazonesmentioning

confidence: 98%

Five‐Membered Heterocycles with Three Heteroatoms: Triazoles

Yet

2011

Modern Heterocyclic Chemistry

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“…Other research groups [40][41][42][43][44][45] amidrazones are accompanied by formazans, especially when excess hydrazine is employed [46].…”

Section: Synthesis Of Hydrazonates From Imidatesmentioning

confidence: 99%

The Chemistry of Hydrazonates

Shawali¹,

Sherif

2007

COC

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The chemistry of esters of hydrazonoic acids has gained increased interest in both synthetic organic chemistry and biological fields. Since a large number of developments in the use of such esters, a review of such developments, covering the literature up to mid 2005, seems to be of considerable value. The present review presents their structural features, nomenclature, synthetic methods and chemical reactions. The utility of the latter reactions for synthesis of various heterocyclic ring systems including mono-, bi-, tri-, tetra-, and penta-heterocycles. In addition, their silicon chelates and biological applications are presented.

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“…3-[(Ethoxycarbonyl)methyl]-1-methyl-4-phenacyl-1,2,4triazolium bromide (2a). Adopting the procedure described in [33], methylhydrazine (4.60 g, 100 mmol) was added with stirring and ice-cooling to a suspension of ethyl 2-(ethoxycarbonyl)acetimidate hydrochloride (19.5 g, 100 mmol) [34] in dry pyridine (50 mL). After 2 hours diethyl ether was added and the mixture was kept overnight at 0−5 °C to allow crystallization of 10.7 g (55%) of 2-(ethoxycarbonyl)-N 2 -methylacetamidrazone hydrochloride (3a) ,48.93;H,4.93;N,11.41.…”

Section: Mar-apr 2007mentioning

confidence: 99%

A new series of non‐classical type C heteropentalenes: 2H‐pyrrolo[2,1‐c][1,2,4]triazoles

Moderhack¹,

Schneider²

2007

Journal of Heterocyclic Chem

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7‐Functionalized title compounds 5 are obtained by cyclization of 3‐acetonyl‐ or 3‐[(alkoxycarbonyl)‐methyl]‐4‐phenacyl‐1,2,4‐triazolium salts 2 having methyl at C(5) the process can be effected in an acetate buffer or by base, irrespective of the function at C(3). 5‐Unsubstituted salts 2 do not react unless the side chain at C(3) is an acetonyl group. Cyclization of 2 with acetic anhydride‐base gives rise to 5,7‐difunctionalized compounds 8; again methyl at C(5) of 2 is compulsory, but here the reaction can be extended to salts having an (alkoxycarbonyl)methyl group at C(4). Regarding defunctionalization, acetyl groups can be split from C(5) only, whereas ester functions are removable also from C(7). Title compounds devoid of acceptor groups (XIII) are unstable but can be trapped by electrophilic reagents (DMAD, acetic anhydride, and phenyl isocyanate) to give the derivatives 10 and 12. The 7‐functionalized products 5 are likewise susceptible to SE‐reactions. By comparison, all title compounds appear to be more reactive toward this kind of reagents than the isomeric 1H‐pyrrolotriazoles (13) including 2H‐pyrrolotetrazoles (III). This is consistent with B3LYP‐DFT calculations using appropriate models.

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Triazoles. Part III. Mono- and di-methyl(phenyl)-1 : 2 : 4-triazoles

Cited by 46 publications

References 0 publications

Five‐Membered Heterocycles with Three Heteroatoms: Triazoles

Five‐Membered Heterocycles with Three Heteroatoms: Triazoles

The Chemistry of Hydrazonates

A new series of non‐classical type C heteropentalenes: 2H‐pyrrolo[2,1‐c][1,2,4]triazoles

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