Unusual rearrangement of spiro β-lactams to 1,4-diazabicyclo[4,4,0] decanes and 1,4-diazabicyclo[4,3,0]nonanes. Synthesis of conformationally restricted σ-receptor ligands

Tetrahedron Letters

Volumn 45, Issue 24, 2004, Pages 4657-4660

  Macías, Alberto ^a   Alonso, Eduardo ^a   Del Pozo, Carlos ^a   González, Javier ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Receptors; 1,4 Diazabicyclo 4,3,0 nonanes; 1,4 Diazabicyclo 4,4,0 decanes; Rearrangement; Retro Mannich reactions; Spiro lactams

Indexed keywords

ALKANE DERIVATIVE; BETA LACTAM; HETEROCYCLIC COMPOUND; SIGMA RECEPTOR LIGAND;

ARTICLE; CALCULATION; CONFORMATION; CYCLOADDITION; DRUG SYNTHESIS; MANNICH REACTION; NUCLEAR OVERHAUSER EFFECT; RACEMIZATION; STEREOCHEMISTRY; THEORETICAL MODEL;

EID: 2442662578     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.109     Document Type: Article

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12. 1H NMR analysis of the reaction crude
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20. The calculations were carried out with the program GAUSSIAN 98 was used: Gaussian 98, Revision A.11.3, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Rega, N.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A.; Gaussian, Inc., Pittsburgh PA, 2002
21. -1)
22. The total energies (hartrees) of the stationary points located are as follows: G (-571.99028), I (-571.97635), H (-571.99604)