Understanding the high reactivity of triazolinediones in Diels-Alder reactions. A DFT study

Journal of Molecular Modeling

Volumn 20, Issue 4, 2014, Pages

  Fernández Herrera, María A ^a   Zavala Oseguera, Claudia ^b   Cabellos, José Luis ^b   Sandoval Ramírez, Jesús ^a   Domingo, Luis R ^c   Merino, Gabriel ^b  

^a BENEMÉRITA UNIVERSIDAD AUTÓNOMA DE PUEBLA   (Mexico)

^b DEPARTAMENTO DE FÍSICA APLICADA   (Mexico)

^c UNIVERSITY OF VALENCIA   (Spain)

Author keywords

DFT study; Polar Diels Alder reaction; Steroidal diene; TADs

Indexed keywords

ELECTROPHILE; STEROID; TRIAZOLINE DERIVATIVE; SOLVENT; TRIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL MODEL; DENSITY FUNCTIONAL THEORY; DIELS ALDER REACTION; ELECTROPHILICITY; ENERGY TRANSFER; PRIORITY JOURNAL; SOLVENT EFFECT; CHEMICAL STRUCTURE; CHEMISTRY;

ALNUS;

MODELS, CHEMICAL; MODELS, MOLECULAR; SOLVENTS; TRIAZOLES;

EID: 84897122496     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-014-2207-7     Document Type: Article

References (32)

1. Mallakpour SE, Butler GB (1989) Modification of polymers via electrophilic aromatic-substitution. J Polym Sci A Polym Chem 27:125-138
2. Mallakpour SE, Butler GB (1989) Uncatalyzed polymerization of bistriazolinediones with electron-rich aromatic-compounds via electrophilic aromatic-substitution. J Polym Sci A Polym Chem 27:217-235
3. Klindert T, Seitz G (1996) 4-Phenyl-1,2,4-triazoline-3,5-dione: a novel dehydrogenating agent for dihydropyridazines. Synth Commun 26:2587-2596 (Pubitemid 26201819)
4. Cookson RC, Gupte SS, Stevens IDR, Watts CT (1988) 4-Phenyl-1,2,4- triazoline-3,5-dione. Org Synth Coll 6:936-940
5. Borhani DW, Greene FD (1986) Triazolinediones - conversion to deaza dimers by electron-transfer catalysis - a possible radical-anion diels-alder reaction. J Org Chem 51:1563-1570
6. Christoforou A, Nicolaou G, Elemes Y (2006) N-phenyltriazolinedione as an efficient, selective, and reusable reagent for the oxidation of thiols to disulfides. Tetrahedron Lett 47:9211-9213 (Pubitemid 44779726)
7. Bazgir A, Seyyedhamzeh M, Yasaei Z, Mirzaei P (2007) A novel three-component method for the synthesis of triazolo 1,2-a indazoletriones. Tetrahedron Lett 48:8790-8794 (Pubitemid 350088055)
8. Cases M, Duran M, Mestres J, Martin N, Sola M (2001) Mechanism of the addition reaction of alkyl azides to 60 fullerene and the subsequent N-2 extrusion to form monoimino- 60 fullerenes. J Org Chem 66:433-442 (Pubitemid 32105558)
9. Elemes Y, Foote CS (1992) Stepwise mechanisms in the ene reaction of alpha, beta-unsaturated esters with N-phenyl-1,2,4-triazoline-3,5-dione and singlet oxygen-intermolecular primary and secondary hydrogen isotope effects. J Am Chem Soc 114:6044-6050
10. Garner P, Ho WB, Grandhee SK, Youngs WJ, Kennedy VO (1991) Development of an asymmetric approach to the 3,8-diazabicyclo 3.2.1 octane moiety of quinocarcin via intermolecular 1,3-dipolar cycloadditions of photochemically generated azomethine ylides. J Org Chem 56:5893-5903
11. Jensen F, Foote CS (1987) Reaction of 4-phenyl-1,2,4-triazoline-3,5-dione with substituted butadienes - a nonconcerted Diels-Alder reaction. J Am Chem Soc 109:6376-6385
12. Lai YC, Mallakpour SE, Butler GB, Palenik GJ (1985) Diels-Alder and ene reactions of 4-substituted 1,2,4-triazoline-3,5-diones and some substituted styrenes. J Org Chem 50:4378-4381
13. Anastassiou AG, Yakali E (1972) Generation and thermal bond relocation of cyclononatetraenyl cation. J Chem Soc Chem Commun 2:92
14. Kobal VM, Gibson DT, Davis RE, Garza DA (1973) X-ray determination of absolute stereochemistry of initial oxidation-product formed from toluene by pseudomonas-pptida 39/D. J Am Chem Soc 95:4420-4421
15. Poutsma ML, Ibarbia PA (1971) Electrophilic additions to 2-methyl-1-(tetramethylcyclopropyliden)propene - generation of cyclopropylidenecarbinyl cations. J Am Chem Soc 93:440
16. Barton DHR, Gunatilaka AAL, Nakanishi T, Patin H, Widdowson DA, Worth BR (1976) Synthetic uses of steroidal ring B diene protection - 22,23-dihydroergosterol. J Chem Soc Perkin Trans 1(8):821-826
17. Fernandez-Herrera MA, Sandoval-Ramirez J, Montiel-Smith S, Meza-Reyes S (2013) A convenient methodology for the in situ oxidation of 4-substituted urazoles. Setting up a one-pot procedure for the efficient protection of dienes. Heterocycles 87:571-582
18. Domingo LR, Sáez JA (2009) Understanding the mechanism of polar Diels-Alder reactions. Org Biomol Chem 7:3576-3583
19. Parr RG, Von Szentpaly L, Liu SB (1999) Electrophilicity index. J Am Chem Soc 121:1922-1924
20. Domingo LR, Chamorro E, Perez P (2008) Understanding the reactivity of captodative ethylenes in polar cycloaddition reactions. A theoretical study. J Org Chem 73:4615-4624 (Pubitemid 351842480)
21. Zhao Y, Schultz NE, Truhlar DG (2006) Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions. J Chem Theory Comput 2:364-382
22. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, Revision C.01. Wallingford, CT
23. Fukui K (1981) The path of chemical-reactions - the IRC approach. Acc Chem Res 14:363-368
24. Marenich AV, Cramer CJ, Truhlar DG (2009) Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. J Phys Chem B 113:6378-6396
25. Parr RG, Pearson RG (1983) Absolute hardness - companion parameter to absolute electronegativity. J Am Chem Soc 105:7512-7516
26. Parr RG, Yang W (1989) Density functional theory of atoms and molecules. Oxford University Press, New York
27. Kohn W, Sham LJ (1965) Self-consistent equations including exchange and correlation effects. Phys Rev 140:1133-1138
28. Chen JS, Houk KN, Foote CS (1998) Theoretical study of the concerted and stepwise mechanisms of triazolinedione Diels-Alder reactions. J Am Chem Soc 120:12303-12309 (Pubitemid 28558189)
29. Sauer J, Schroder B (1965) Reactivity of dienophiles and ability to form charge-transfer complexes. Angew Chem Int Ed 4:711
30. Sauer J (1967) Diels-Alder reactions 2 - reaction mechanism. Angew Chem Int Ed 6:16
31. Domingo LR, Aurell MJ, Perez P, Contreras R (2002) Quantitative characterization of the global electrophilicity power of common diene/dienophile pairs in Diels-Alder reactions. Tetrahedron 58:4417-4423 (Pubitemid 34522034)
32. Jaramillo P, Domingo LR, Chamorro E, Perez P (2008) A further exploration of a nucleophilicity index based on the gas-phaseionization potentials. J Mol Struct THEOCHEM 865:68-72