Azohydrazone Conversion. II. The Coupling of Diazonium Ion with β-Diketones

Yao, Hua

doi:10.1021/jo01033a037

Cited by 113 publications

(63 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The results of elemental analyses and the mass spectra of the products were consistent with 14A and its isomeric structure 14B. The product was assigned structure 14B since the hydrazone structure 14A was excluded depending on their electronic spectra as they revealed a characteristic absorption maxima at λmax 361 (log ε 4.43) and λ 400 (log ε 4.40) assignable to arylazo chromophore (Burawoy et al, 1952;Yao, 1964;Yao & Resnick, 1962). The correct structure 14B was further evidenced by spectroscopic data.…”

Section: Resultsmentioning

confidence: 53%

Synthesis of New Derivatives of Heterocyclic Compounds Containing Pyridine, Pyrimidine and Triazole Ortho-Fused to Isoquinoline Moiety

Abunada¹,

Hassaneen²,

Miqdad³

2012

IJC

View full text Add to dashboard Cite

Abstract4-Amino-9,10-dimethoxy-2-phenyl-6,7-dihydro-2(H)-pyrido[2,1-a]isoquinoline-1,3-dicarbonitrile derivatives 4a-c were obtained from the reaction of 6,7-dimethoxy-3,4-dihydroisoqinoline-1-acetonitrile 1 with arylidenemalononitrile 2a-c in boiling acetonitile in the presence of piperidine. The reaction of 4a-c with triethyl orthoformate in acetic anhydride at reflux give the ethoxymethyleneamino derivatives 5a-c. Compounds 5a-c were reacted with hydrazine hydrate and give the corresponding 4-amino-3-imino-2-aryl-3,4,8,9-tetrahydro-2(H)-pyrimido[5′,4′:5,6] pyrido [2,1-a]isoquinoline-1-carbonitrile derivatives 6a-c. Refluxing compound 6a in an excess of triethyl orthoformate give 7a. When compounds 6a-c were refluxed with acetic anhydride or benzoyl chloride in pyridine, they afford the corresponding 4-methyl and 4-phenyl derivatives 8a-c and 9a-c, respectively. Compound 6a was refluxed in diethyloxalate and give product 10. Also, the reaction of 6a with C-acylhydrazonoyl halides 13a,b in refluxing chloroform in the presence of triethylamine afford 14a,b. Correct elemental analyses and spectral data (IR, 1 H NMR, 13 C NMR and MS) confirm the structure of the synthesized compounds.

show abstract

Section: Resultsmentioning

confidence: 53%

Synthesis of New Derivatives of Heterocyclic Compounds Containing Pyridine, Pyrimidine and Triazole Ortho-Fused to Isoquinoline Moiety

Abunada¹,

Hassaneen²,

Miqdad³

2012

IJC

View full text Add to dashboard Cite

show abstract

“…In contrast to azo compounds, a weak absorption band (or no band) for hydrazones is located at 284 to 295 nm and a strong absorption band is observed at 390-320 nm, which distinguishes these two types of compounds. 34 It is worth noting that this absorption is shifted to higher wavelength in the case of the E-isomer in comparison with the Z-isomer, possibly due to the different hydrogen bonding in both isomers.…”

Section: 33mentioning

confidence: 94%

Synthesis and properties of hydrazones bearing amide, thioamide and amidine functions

Belskaya¹,

Dehaen²,

Бакулев³

2010

Arkivoc

113

View full text Add to dashboard Cite

This review provides detailed methods for the synthesis, structures and chemical properties of hydrazones bearing carboxamide, thioamide and amidine functions. The main accent was put on the cyclization reactions leading to pyrazoles, thiazoles, 1,2,3-triazoles, 1,2,3-thiadiazoles, 1,2,4-triazines and other heterocyclic compounds. In addition, we have reviewed methods for the synthesis of substrates for pericyclic reactions from the hydrazones.

show abstract

“…The azo compounds have a strong band at 270-280 nm. The monophenyl-hydrazones give aweak absorption band (or no band) in this region and a strong absorption band at a wave length higher than 320 nm 11 . 12 .…”

Section: Hn^^n Rmentioning

confidence: 99%

“…Compared with the CO absorption of the parent compound 3a (vCO 1770 cm" 1 ), the CO of 5a has undergone a shift to lower frequency. Such a shift can be attributed to conjugation with the C=N double bond 11 .…”

Section: Hn^^n Rmentioning

confidence: 99%

Reactions with 5,6,7-Trihydro-5,7-diarylthiazolo [3,2-b] -s-triazin-3(2 H)-ones

Soliman

1976

Zeitschrift Für Naturforschung B

View full text Add to dashboard Cite

Condensation of thiourea with ammonium acetate or amine and aldehyde gives hexahydro-s-triazine-2-thiones 1-4 .4,6-Diarylhexahydro-s-triazine-2-thiones (1) which were prepared by AHMED and RAO 4 reacted with chloroacetic acid to give the corresponding 4,6-diaryl-2-carboxymethylthio-3,4,5,6-tetrahydro-s-triazines (2). Cyclisation of 2 by the action of acetic anhydride in acetic acid yields products which are formulated as 5,6,7-trihydro-5,7-diarylthiazolo[3,2-b]-s-triazin-3(2H)-ones (3). HN^^N rThe IR spectrum (KBr) of 3 a shows an intense CO band at 1770 cm -1 . This carbonyl frequency is rather high; however, it has been noted that a carbonyl group attached to a triazole and a triazine rings shows unusually high stretching frequency [5][6][7][8] . The NMR spectrum (DMSO-d6) of 3 a, shows a methylene group (s, 2H) at r 5.27 ppm. These facts indicate that the products 3 exist in the keto form, and not as the hydroxy form.The methylene group of compound 3 was found to condense with aromatic aldehydes to give 2-arylmethylene -5,6,7-trihydro -5,7-diary lthiazolo[3,2 -b] -s-triazin-3(2H)-ones (4). These arylmethylene derivatives were better prepared directly from the hexahydrotriazine-thiones by the action of chloroacetic acid, the aromatic aldehyde in the presence of acetic acid, acetic anhydride and sodium acetate. The carboxymethylthio-tetrahydrotriazines (2) also reacted with the remaining reagents to yield the arylmethylene derivatives (4).The IR spectrum of the arylmethylene derivative (4a) shows a carbonyl absorption at ca. 1730 cm -1 . This CO frequency has been shifted to a lower frequency compared with the CO frequency in 3, due to its conjugation with the exocyclic C=C double bond 9 .

show abstract

Azohydrazone Conversion. II. The Coupling of Diazonium Ion with β-Diketones

Cited by 113 publications

References 2 publications

Synthesis of New Derivatives of Heterocyclic Compounds Containing Pyridine, Pyrimidine and Triazole Ortho-Fused to Isoquinoline Moiety

Synthesis of New Derivatives of Heterocyclic Compounds Containing Pyridine, Pyrimidine and Triazole Ortho-Fused to Isoquinoline Moiety

Synthesis and properties of hydrazones bearing amide, thioamide and amidine functions

Reactions with 5,6,7-Trihydro-5,7-diarylthiazolo [3,2-b] -s-triazin-3(2 H)-ones

Contact Info

Product

Resources

About