Synthesis of phenethylenamides and their radical cyclization to 3- benzazepines

Tetrahedron

Volumn 55, Issue 17, 1999, Pages 5599-5610

  Cid, María Magdalena ^a   Domínguez, Domingo ^b   Castedo, Luis ^b   Vázquez López, Ezequiel M ^a  

^a UNIVERSITY OF VIGO   (Spain)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Benzazepines; Enamides; Radical reactions

Indexed keywords

3 BENZAZEPINE DERIVATIVE; AMIDE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033597241     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00225-2     Document Type: Article

References (15)

1. [1] Gözler B, The Alkaloids,. A. Brossi editor, NY: Academic Press, 1987; 31: 317-389.
2. [2] Blaskó G, The Alkaloids, A. Brossi editor, NY: Academic Press, 1990; 38: 157-224.
3. [3] Boente JM, Castedo L, Domínguez D, Ferro M, Tetrahedron Lett. 1986; 27: 4077-4078.
4. [4] Valencia E, Freyer J, Shamma M, Fajardo V, Tetrahedron Lett. 1984; 25: 599-602.
5. [5] Huang L, Xue Z, The Alkaloids, A. Brossi editor, NY: Academic Press, 1984; 23: 157-226.
6. [6] Fidalgo J, Castedo L, Domínguez D, Tetrahedron Lett. 1993; 34: 7317-7318.
7. [7] Rodríguez G, Cid MM, Saá C, Castedo L, Domínguez D, J. Org. Chem. 1996; 61: 2780-2782.
8. [8] This method was used in the work described in ref. 7. A similar method using TBAF as catalyst, has been used to synthesize cyclic enamides from acetetylenic amides: Jacobi PA, Brielmann HL, Hauck SI, J. Org. Chem. 1996; 61: 5013-5023.
9. [9] Uskokovic M, Gut M, Helvetica Chimica Acta, 1959; 42: 2258-2261.
10. [10] Compound 5 has been synthesized in high yield by tandem carbophilic addition-N-acyliminium ion cyclization of a N-phenethylimides: Collado MI,. Manteca I, Sotomayor N, Villa MJ, Lete E, J. Org. Chem. 1997; 62: 2080-2092.
11. [11] Atomic coordinates, bond lengths, and angles, and thermal parameters for compound 12d have been deposited at the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2, 1EZ, UK.
12. [12] Tse I, Snieckus V, J. Chem. Soc., Chem. Commun. 1976: 505-506
13. [13] Sheldrick GM, Acta Cryst. 1990; A46: 467-473.
14. [14] Sheldrick GM, SHELXL97. Program for the Refinement of Crystal Structures. University of Göttingen, Germany.
15. [15] International Tables for Crystallography, Vol C, Kluwer, Dordrecht, 1993: Tables 4.2.6.8 and 6.1.1.4.