Condensation of amino azoles with benzocycloalkanones and dimethylformamide

Десенко, С. М.; Orlov, V. D.; Estrada, Jess; Ivkov, S. M.

doi:10.1007/bf00474009

Cited by 6 publications

(9 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A. Compound 10 was synthesized analogously to compound 3a from azoloazine 1 and 2,3 dibromo 1,3 di phenylpropan 1 one (9). The yield was 28%, m.p.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and chemical transformations of partially hydrogenated [1,2,4]triazolo[5,1-b]quinazolines

et al. 2006

Self Cite

View full text Add to dashboard Cite

The reaction of 5 methyl 7 phenyl 4,7 dihydro 1,2,4 triazolo[1,5 a]pyrimidine with α,β unsaturated carbonyl compounds in MeOH in the presence of MeONa affords partially hydrogenated aryl substituted [1,2,4]triazolo[5,1 b]quinazolines. Hydrolysis, oxidation, re duction, and alkylation of 5,6,8 triphenyl 5,6,7,10 tetrahydro[1,2,4]triazolo[5,1 b]quinazoline were studied. The structure of one oxidation product, viz., 7 hydroxy 5,6,8 triphenyl 6,7 dihydro[1,2,4]triazolo[5,1 b]quinazoline, was established by X ray diffraction.Partially hydrogenated quinazoline systems have at tracted interest from both fundamental and applied points of view. Most structures of this type belong to so called drug like molecules or are present in natural biologically active compounds, for example, in alkaloids. 1 Adenosine uptake inhibitors (potent vasodilators and antiaggre gants) 2,3 and carbocyclic purine analogs exhibiting anti metabolic activity were found in the azoloquinazoline series. 4 At the same time, these compounds are conve nient models for elucidating some questions of theoreti cal organic chemistry, in particular, the characteristic fea tures of the three dimensional and electronic structures of partially hydrogenated nitrogen containing hetero cycles, their stability, and reactivity.There are two main procedures for the formation of azoloquinazoline systems. The most widely used proce dure is based on the construction of the pyrimidine ring in reactions of α aminoazole derivatives with carbonyl 1,3 bielectrophiles containing a partially or completely hy drogenated carbocycle. 5-12 A nontrivial procedure has been developed earlier for the assembly of 2 methyl 5,10 diphenyl 5,10 dihydro[1,2,4]triazolo[5,1 b]quinazolines based on the cascade reaction giving rise to both the triazole and quinazoline fragments. 13 However, the pyri midine ring closure in this process is also preceded by the formation of the aminotriazole fragment. An alternative approach to the desired compounds is associated with the formation of the five membered azole ring based on the already present quinazoline moiety, but this method is synthetically more limited. 14 Recently, 15 we have described yet another procedure for the synthesis of [1,2,4]triazolo[5,1 b]quinazolines, which differs from the above mentioned methods in that the carbocycle closure occurs on the basis of the already present partially hydro genated 5 methyl 7 phenyl 1,2,4 triazolo[1,5 a]pyrimi dine system with the involvement of 1,3 diaryl 2 propen 1 ones in an alcoholic medium in the presence of MeONa.The aim of the present study was to extend the range of carbonyl 1,3 bielectrophiles, which react with 5 me thyl 7 phenyl 4,7 dihydro 1,2,4 triazolo[1,5 a]pyrimi dine (1) to give partially hydrogenated [1,2,4]triazo lo[5,1 b]quinazoline systems (Scheme 1), and to study the chemical behavior of the latter in hydrolysis, oxida tion, reduction, and alkylation reactions.It was found that refluxing of equimolar amounts of carbonyl 1,3 bielectrophiles 2a,b, 4, 6, 9, and 11 with dihydrotriazolo...

show abstract

“…A. Compound 10 was synthesized analogously to compound 3a from azoloazine 1 and 2,3 dibromo 1,3 di phenylpropan 1 one (9). The yield was 28%, m.p.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and chemical transformations of partially hydrogenated [1,2,4]triazolo[5,1-b]quinazolines

et al. 2006

Self Cite

View full text Add to dashboard Cite

show abstract

“…1 H NMR spectrum, δ, ppm: 9. 44, 9.54, 9.95 -8-phenyl-3a,4,5,6,7,8,9,9a-octahydro[1,2,4]triazolo[3,4-b]quinazoline (5b) were synthesized analogously in 82% yield; mp 228-230°C (DMF) [2]. 1 H NMR spectrum, δ, ppm: 9.39, 9.00 (1H, s, NH); 5.79 (1H, s, H-4); 5.64 (1H, s, H-8); 1.91-2.08 (2H, m, H-5); 1.59-1.74 (2H, m, H-6); 2.08-2.78 (2H, m, H-7); 7.41 (1H, s, H-2); 6.98-7.57 (10H, m, H Ar).…”

mentioning

confidence: 99%

First example of reaction of asymmetric dienone derivatives of cyclohexane with 3-amino- 1,2,4-triazole. Formation of isomeric octahydrotriazoloquinazolines

Varshalomidze

Golikov

Кривенько

2009

Chem Heterocycl Comp

View full text Add to dashboard Cite

“…The synthesis of 6- [4-(N- The 4-acetylaminophenylacetic acid (15), subjected to Vilsmeier-Haack condensation [13], was hydrolyzed in the acidic medium of the reaction mixture and the resulting ammonium ion was N-formylated to afford the 3-dimethylamino-2-[4-(N-formyl)aminophenyl]-2-propenal ( 16). This compound deteriorates considerably on standing with formation of tar products, so it was quickly used without purification in the following step.…”

mentioning

confidence: 99%

“…Finally, N-acetylation of 19 easily provided the expected compound 20. These tetracyclic compounds, which might be considered conformationally restricted analogues of compounds 7 and 8, appear hitherto not to have been extensively studied, as only three references related to their preparation by different synthetical pathways are reported in the chemical literature [14][15][16].…”

mentioning

confidence: 99%

“…Calcd. for C16 H 16 N 4 O: C, 68.55; H, 5.75; N, 19.99. Found: C, 68.66; H, 5.60; N, 20.18. q, 2H, N-CH 2 ), 1.93 (bs, 3H, acetyl CH 3 ), 1.14 (t, 3H, N-ethyl CH 3 ); 13 C-nmr (deuteriochloroform): δ 169.8 (acetyl C=O), 164.2 (CONH 2), 151.1 (C-5), 147.8 (C-3a), 147.3 (C-7), 147.1 (C-2), 146.2 (C-4'), 131.1 (C-2' and C-6'), 129.4 (C-1'), 128.8 (C-3' and C-5'), 108.8 (C-6), 105.6 (C-3), 44.6 (N-CH 2 ), 23.3 (acetyl CH 3 ), 13.6 (N-ethyl CH 3 ); ms: (m/z) 323 (M + ), 295, 281, 266, 249, 237.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of pyrazolo[1,5‐a]‐, 1,2,4‐triazolo[1,5‐a]‐ and imidazo[1,2‐a]pyrimidines related to zaleplon, a new drug for the treatment of insomnia

Mustazza

Giudice

Borioni

et al. 2001

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

Condensation of amino azoles with benzocycloalkanones and dimethylformamide

Cited by 6 publications

References 1 publication

Synthesis and chemical transformations of partially hydrogenated [1,2,4]triazolo[5,1-b]quinazolines

Synthesis and chemical transformations of partially hydrogenated [1,2,4]triazolo[5,1-b]quinazolines

First example of reaction of asymmetric dienone derivatives of cyclohexane with 3-amino- 1,2,4-triazole. Formation of isomeric octahydrotriazoloquinazolines

Synthesis of pyrazolo[1,5‐a]‐, 1,2,4‐triazolo[1,5‐a]‐ and imidazo[1,2‐a]pyrimidines related to zaleplon, a new drug for the treatment of insomnia

Contact Info

Product

Resources

About