Studies on Spiroheterocycles, Part III: Synthesis of Diazaspiroundecanetetraone Derivatives Containing Biologically Active Heterocycles

Behera, Ratikanta; Behera, Ajay Kumar; Pradhan, Rosy; Pati, Anita

doi:10.1080/10426500802274260

Cited by 9 publications

(11 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In pursuance of our interest in developing methods for the synthesis of new heterocylic systems having potential biological activities , we synthesized tetrahydro‐5(1 H )‐quinolinones 3a , 3b , 3c , 3d , 3e , 3f , 3g , 3h , 3i , 3j , 3k , 3l , 3m , 3n , 3o , 3p , 3q , 3r , 3s , 3t , by the treatment of dimedone with various chalcones 2 and ammonium acatate in the presence of catalytic amount of acetic acid according to the procedure reported in literature (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Para Substituted Benzaldehydes as Expedient Reagents for the Oxidative Aromatization of Hydroquinoline

Majumdar

Pati

Behera

et al. 2013

J. Heterocyclic Chem.

Self Cite

View full text Add to dashboard Cite

A Cannizzaro-type reaction of tetrahydro-5(1H)-quinolinones with para substituted benzaldehydes in the presence of a base formed the corresponding quinoline and aryl methanol rather than arylidene derivatives because of the oxidation of tetrahydroquinoline and reduction of benzaldehydes as a result of unprecedented hydride transfer from tetrahydroquinoline to arylaldehydes. The reaction proceeds best with the participation of substituents with +M effect in substrate molecule.

show abstract

Section: Resultsmentioning

confidence: 99%

Para Substituted Benzaldehydes as Expedient Reagents for the Oxidative Aromatization of Hydroquinoline

Majumdar

Pati

Behera

et al. 2013

J. Heterocyclic Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…We noted that, the Cl2 and Cl4 atoms are in close contact to O8-atom where the Cl-O intramolecular distance is predicted around 3.3 Å. This could explain the different natural charges at [11][12] 1.394 1.381 A(10-48-50) 109.7 109.5 R (11)(12)(13)(14)(15)(16)(17)(18)(19) 1.404 1.399 A(10-48-51) 109.7 109.5 R 12-141.387 1.364 A (12-11-19) 122.2 121.8 R 14-151.390 1.369 A (11-12-14) 119.2 119.4 R 15-171.389 1.386 A (11-19-17) 116.3 116.1 R(17- 19) 1.404 1.392 A (11-19-20) 122 . [11][12] 116.1 116.9 A (26-29-35) 111.1 110.9 A(1- [11][12][13][14][15][16][17][18][19] 121.7 121.3 A (31-29-35) 114.3 115.6 A(2- 119.3 119.5 A (29-31-32) 111.0 114.5 A (2-14-15) 119.9 118.9 A (29-31-34) 105.9 107.8 A(3- 121.7 120.7 A (29-35-36) 122.7 120.7 A(3- [36][37] 116.1 116.3 A (29-35-42) 121.0 124.0 A (4-39-37) 119.3 118.8 A (32-31-34) 115.1 114.0 A (4-39-40) 119.9 120.3 A (36-35-42) 116.3 115.3 A (5-25-22) 122.2 121.4 A (35-36-37) 122.2 123.0 A (5-25-26) 122.2 120.8 A (35-42-40)...…”

Section: Natural Atomic Chargementioning

confidence: 99%

“…They also act as nicotinic receptor antagonists and possess antibiotic, antimicrobial and anticancer properties. [4][5][6][7][8][9][10] However, current literature reveals that some diazaspiro [5.5]undecane-1,3,5,9tetraones motif possess a variety of therapeutic and biological properties such as anticonvulsant, 11 antifungicidal, 12 potent sedative-hypnotic, 13 antibacterial 14 and CNS depressant properties. 15 Moreover, this type of compounds can also be used as a yellow organic pigment and as a disperse dye with strong fluorescence property as it contains barbituric acid moiety.…”

Section: Introductionmentioning

confidence: 99%

Crystal Structure of 7,11-bis(2,4-dichlorophenyl)-2,4-dimethyl-2,4- diazaspiro[5.5]undecane -1,3,5,9-tetraone and its computational studies

et al. 2015

View full text Add to dashboard Cite

Crystals of 7,11-bis(2,4-dichlorophenyl)-2,4-dimethyl-2,4-diazaspiro[5.5]undecane-1,3,5,9tetraone were grown in polar solvents and subjected to single crystal X-ray diffraction. The molecular crystal is Triclinic, P-1, a = 8.3734 (19) Å, b = 12.382 (3) Å, c = 12.871 (3) Å, α = 66.639 (7) • , β = 85.148 (7) • , γ = 70.690 (6) • , V = 1154.5 (5)Å 3 , Z = 2, D calc = 1.519 g cm −3. The optimized molecular structure of the studied compound using B3LYP/6-311G(d,p) method showed good agreement with the X-ray structure. The electronic and spectroscopic properties of the title compound were predicted. The NBO calculations were used to calculate the natural atomic charges at the different atomic sites as well as the intramolecular charge transfer (ICT) interactions among the most significant natural orbitals. The high LP(N)→ BD*(2)C-O ICT interaction energies indicate strong electron delocalization from the lone pair of the N-atoms of the pyrimidinetrione ring to the adjacent carbonyl groups. In contrast, the small LP(O)→BD*(1)C-H stabilization energies (E (2)) indicated weak C-H-O interactions. Experimentally, the studied compound showed the most intense electronic transition band at 232 nm which is calculated using TD-DFT method as a shoulder at 231.3 nm (f=0.0832) and it belongs to H-3/H-1→L+1 and H-2→L+2 excitations. The GIAO calculated 1 H and 13 C NMR chemical shifts showed good correlations with the experimental data.

show abstract

“…Beside the biological importance, these spirocycles have been extensively used for the synthesis of novel ligands, catalysts and some special organic optoelectronics synthetic materials (Saragi et al, 2007;Xie and Zhou, 2008;Ding et al, 2009). In addition, recent literature review suggests that the diazaspiro [5.5]undecane-1,3,5,9-tetraones motif has a wide range of therapeutic and biological properties such as CNS depressant , anticonvulsant (Rajopadhye and Popp, 1988), potent sedative-hypnotic (Kesharwani et al, 2009), antibacterial (Goel et al, 2005) and fungicidal (Behera et al, 2009). Moreover, these types of compounds can also be used as a yellow organic pigment and as a disperse dye with strong fluorescence property as it contains barbituric acid moiety (Theford et al, 2003;Karci, 2008;Wang and Kim, 2009).…”

Section: Introductionmentioning

confidence: 98%

Stereoselective synthesis of diazaspiro[5.5]undecane derivatives via base promoted [5+1] double Michael addition of N,N-dimethylbarbituric acid to diaryliedene acetones

Islam

Barakat

Al‐Majid

et al. 2017

Arabian Journal of Chemistry

View full text Add to dashboard Cite

The nitrogen containing spiro-heterocycle is one of the privileged synthetic motif that constitutes various naturally occurring molecules and displays a broad range of pharmaceutical and biological activities. A new methodology was developed for the synthesis of 2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraones spiro-heterocyclic derivatives via cascade cyclization of [5+1] double Michael addition reaction of N,N-dimethylbarbituric acid with the derivatives of diaryldivinylketones in the presence of diethylamine at ambient temperature. The developed protocol is highly capable of furnishing diazaspiro[5.5]undecane derivatives 3a-m in excellent yields (up to 98%), from easily accessible symmetric and non-symmetric divinylketones 2a-m, containing aryl and heteroaryl substituents. The diazaspiro-heterocyclic structure was mainly elucidated by NMR and X-ray crystallographic techniques. The single-crystal X-ray studies revealed that, the

show abstract

Studies on Spiroheterocycles, Part III: Synthesis of Diazaspiroundecanetetraone Derivatives Containing Biologically Active Heterocycles

Cited by 9 publications

References 16 publications

Para Substituted Benzaldehydes as Expedient Reagents for the Oxidative Aromatization of Hydroquinoline

Para Substituted Benzaldehydes as Expedient Reagents for the Oxidative Aromatization of Hydroquinoline

Crystal Structure of 7,11-bis(2,4-dichlorophenyl)-2,4-dimethyl-2,4- diazaspiro[5.5]undecane -1,3,5,9-tetraone and its computational studies

Stereoselective synthesis of diazaspiro[5.5]undecane derivatives via base promoted [5+1] double Michael addition of N,N-dimethylbarbituric acid to diaryliedene acetones

Contact Info

Product

Resources

About