Triazines and related products. Part X. A re-examination of the reaction between benzil and diaminoguanidine nitrate

M F G Stevens

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Abstract

Benzil reacts with diaminoguanidine nitrate to yield the nitrate salt of benzil mono[(aminoamidino)hydrazone] (2). The hydrazone (2) is unstable, and cyclises on melting or in solvents to 5,6-diphenyl-3-hydrazino-1,2,4-triazine (3). Diazotisation of the hydrazone (2) and of hydrazine (3) affords the same product, 6,7-diphenyltetrazolo-[1,5-b]-as-triazine (9) which decomposes in boiling secondary amines to yield substituted 3-amino-5,6-diphenyl-1,2,4- triazines and hydrazoic acid. Both the hydrazone (2) and the hydrazine (3) react with triethyl orthoformate or formic acid to give 6,7-diphenyltriazolo[4,3-b]- as-triazine (16), which was also prepared, unambiguously, from benzil and 3,4-diamino-1,2,4-triazole. Although conditions favourable for Dimroth rearrangement were employed, no such transformations were encountered in the reactions of the bicyclic systems (9) and (16).

Original languageEnglish
Pages (from-to)1221-1225
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 1
DOIs
Publication statusPublished - 1972

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Hydrazones
Triazines
hydrazine
Nitrates
formic acid
Boiling liquids
Amines
Melting
Salts
diaminoguanidine
benzil
1,2,4-triazine
diphenyl

Cite this

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title = "Triazines and related products. Part X. A re-examination of the reaction between benzil and diaminoguanidine nitrate",
abstract = "Benzil reacts with diaminoguanidine nitrate to yield the nitrate salt of benzil mono[(aminoamidino)hydrazone] (2). The hydrazone (2) is unstable, and cyclises on melting or in solvents to 5,6-diphenyl-3-hydrazino-1,2,4-triazine (3). Diazotisation of the hydrazone (2) and of hydrazine (3) affords the same product, 6,7-diphenyltetrazolo-[1,5-b]-as-triazine (9) which decomposes in boiling secondary amines to yield substituted 3-amino-5,6-diphenyl-1,2,4- triazines and hydrazoic acid. Both the hydrazone (2) and the hydrazine (3) react with triethyl orthoformate or formic acid to give 6,7-diphenyltriazolo[4,3-b]- as-triazine (16), which was also prepared, unambiguously, from benzil and 3,4-diamino-1,2,4-triazole. Although conditions favourable for Dimroth rearrangement were employed, no such transformations were encountered in the reactions of the bicyclic systems (9) and (16).",
author = "Stevens, {M F G}",
year = "1972",
doi = "10.1039/P19720001221",
language = "English",
pages = "1221--1225",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
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T1 - Triazines and related products. Part X. A re-examination of the reaction between benzil and diaminoguanidine nitrate

AU - Stevens, M F G

PY - 1972

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N2 - Benzil reacts with diaminoguanidine nitrate to yield the nitrate salt of benzil mono[(aminoamidino)hydrazone] (2). The hydrazone (2) is unstable, and cyclises on melting or in solvents to 5,6-diphenyl-3-hydrazino-1,2,4-triazine (3). Diazotisation of the hydrazone (2) and of hydrazine (3) affords the same product, 6,7-diphenyltetrazolo-[1,5-b]-as-triazine (9) which decomposes in boiling secondary amines to yield substituted 3-amino-5,6-diphenyl-1,2,4- triazines and hydrazoic acid. Both the hydrazone (2) and the hydrazine (3) react with triethyl orthoformate or formic acid to give 6,7-diphenyltriazolo[4,3-b]- as-triazine (16), which was also prepared, unambiguously, from benzil and 3,4-diamino-1,2,4-triazole. Although conditions favourable for Dimroth rearrangement were employed, no such transformations were encountered in the reactions of the bicyclic systems (9) and (16).

AB - Benzil reacts with diaminoguanidine nitrate to yield the nitrate salt of benzil mono[(aminoamidino)hydrazone] (2). The hydrazone (2) is unstable, and cyclises on melting or in solvents to 5,6-diphenyl-3-hydrazino-1,2,4-triazine (3). Diazotisation of the hydrazone (2) and of hydrazine (3) affords the same product, 6,7-diphenyltetrazolo-[1,5-b]-as-triazine (9) which decomposes in boiling secondary amines to yield substituted 3-amino-5,6-diphenyl-1,2,4- triazines and hydrazoic acid. Both the hydrazone (2) and the hydrazine (3) react with triethyl orthoformate or formic acid to give 6,7-diphenyltriazolo[4,3-b]- as-triazine (16), which was also prepared, unambiguously, from benzil and 3,4-diamino-1,2,4-triazole. Although conditions favourable for Dimroth rearrangement were employed, no such transformations were encountered in the reactions of the bicyclic systems (9) and (16).

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