Synthesis and characterization of dibenzodioxazasiladecines

Synthetic Communications

Volumn 38, Issue 5, 2008, Pages 775-783

  Singh, M S ^a   Singh, Pratibha ^a  

^a BANARAS HINDU UNIVERSITY   (India)

Author keywords

Dianion; Dibenzodioxazasiladecines; Diorganodichlorosilanes; Electrophilic cyclizations; o aminobenzyl alcohol

Indexed keywords

ANION; DIBENZODIOXAZASILADECINE DERIVATIVE; DIBENZODIOXAZOCINE DERIVATIVE; DIORGANODICHLOROSILANE DERIVATIVE; N (2 HYDROXYMETHYLPHENYL)SALICYLIDENEIMINE; SALICYLALDEHYDE; SODIUM; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CYCLIZATION; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; SILICON 29 NUCLEAR MAGNETIC RESONANCE SPECTROMETRY; SYNTHESIS;

EID: 39049140129     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701820608     Document Type: Article

References (34)

1. Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. Enantioselective epoxidation of unfunctionalized olefins catalyzed by (salen) manganese complexes. J. Am. Chem. Soc. 1990, 112, 2801-2803.
2. Irie, R.; Noda, K.; Ito, Y.; Matsumoto, N.; Katsuki, T. Catalytic asymmetric epoxidation of unfunctionalized olefins. Tetrahedron Lett. 1990, 31, 7345-7348.
3. (a) Fukuda, T.; Katsuki, T. Highly enantioselective cyclopropanation of styrene derivatives using Co(III)-Salen complex as a catalyst. Tetrahedron 1997, 53, 7201-7208;
4. (b) Li, Z.; Conser, K. R.; Jacobsen, E. N. Asymmetric alkene aziridination with readily available chiral diimine-based catalysts. J. Am. Chem. Soc. 1993, 115, 5326-5327;
5. (c) Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. Highly enantioselective ring opening of epoxides catalyzed by chiral (salen) Cr(III) complexes. J. Am. Chem. Soc. 1995, 117, 5897-5898.
6. Synthetic catalysts which are enantioselective over a wide range of different reactions were defined as privileged. Yoon, T. P.; Jacobsen, E. N. Privileged chiral catalysts. Science 2003, 299, 1691-1693.
7. Schiff, H. Ann. Suppl. 1864, 3, 343.
8. (a) Layer, R. W. The chemistry of imines. Chem. Rev. 1963, 63, 489-510;
9. (b) Alexander, V. Design and synthesis of macrocyclic ligands and their complexes of lanthanides and actinides. Chem. Rev. 1995, 95, 273-342;
10. (c) Higuchi, M.; Yamamoto, K. Novel cyclic molecules: Selective synthesis of cyclic phenylazomethines. Org. Lett. 1999, 1, 1881-1883.
11. Tanabe, Y.; Nagaosa, M.; Nishii, Y. Syntheses of perhydro-1,3,4- thiadiazin-5-ones and 3-arylaminothiazolidine-4-ones by the regioselective cyclocondensation of 2-sulfanylalkanoic acids or their silyl esters with methyl and aryl hydrazones. Heterocycles 1995, 41, 2033-2042.
12. Gielen, M.; Boualam, M.; Biesemans, M.; Mahieu, B.; Willem, R. Diorganotin derivatives of 2,6-dihydroxymethylpyridine and of 3,5-di(N-pyrrolidino)-1,2-propanediol: Synthesis, characterization and in vitro antitumor activity. Heterocycles 1992, 34, 549-559.
13. Larsen, W.; Corey, J. Y. A pulsed NMR study of molecular motion in solid 6,12,12-trimethyl-5,6-dihydro-7H,12H-dibenzo[c,f][1,5]silazocine. J. Am. Chem. Soc. 1977, 99, 1740-1745.
14. (a) Chandrasekaran, A.; Day, R. O.; Holmes, R. R. Structural influence of a sulfinyl group in eight-membered rings of diorganosilanes. Organometallics 1996, 15, 3182-3188;
15. (b) Crisp, G. T.; Bubner, T. P. Preparation of sterically constrained arylalkynes. Tetrahedron 1997, 53, 11881-11898.
16. Wilkinson, G.; Stone, F. G. A.; Abel, E. W. Comprehensive Organometallic Chemistry; Pergamon Press: Oxford, 1982, p. 2.
17. Bajaj, P.; Mehrotra, R. C. (Aminoalkoxy)silanes, II: Synthesis of vinyl- and phenyl (aminoalkoxy)silanes. J. Organometal. Chem. 1970, 25, 359-365.
18. Malcolm, S.; Pressman, D. The reactions of antiserum homologous to the p-azomaleanilate and p-azofumaranilate ion groups. J. Am. Chem. Soc. 1954, 76, 2863-2866.
19. Thompson, C. M.; Green, D. L. C. Recent advances in dianion chemistry. Tetrahedron 1991, 47, 4223-4285.
20. Green, D. L. C.; Thompson, C. M. New methods and reagents in organic synthesis of fulvalene and its analogues. Tetrahedron 1991, 32, 5051-5070.
21. (a) Thompson, C. M. Dianion Chemistry in Organic Synthesis; CRC Press: Boca Raton: FL, 1994;
22. (b) Langer, P.; Freiberg, W. Cyclization reactions of dianions in organic synthesis. Chem. Rev. 2004, 104, 4125-4150.
23. (a) Singh, M. S.; Singh, A. K. Dioximes as synthons for medium ring heterocyclic compounds. Heterocycles 2000, 53, 851-859;
24. (b) Singh, M. S.; Singh, A. K. Heterocyclization of vicinal dioximes to seven-membered N, P, and O heterocycles. Indian J. Chem. 2000, 39B, 551-553;
25. (c) Singh, M. S.; Pandey, G. A convenient synthetic entry into 2,2-diorganyl-5,6-diaryl-1,3,4,2-dioxadiazasilacyclohexene derivatives via dianion cyclization: Sequential one pot cyclosilylation. Synth. Commun. 2000, 30, 3589-3594.
26. (a) Singh, M. S.; Singh, A. K. Synthesis of novel heterocycles from benzoin α-oxime by reaction with electrophiles. Synthesis 2004, 837-839;
27. (b) Singh, M. S.; Singh, B. K.; Singh, A. K. A facile synthetic approach to cyclic carbonates and thiocarbonates via dianion cyclization. Indian J. Chem. 2002, 41B, 1507-1509;
28. (c) Singh, M. S.; Singh, A. K. Efficient and convenient one-pot synthesis of dioxadiazaphosphepines. Synth. Commun. 2000, 30, 53-61.
29. Singh, M. S.; Singh, A. K. A novel one-pot procedure for the synthesis of stable dioxadiazastannepines and dioxadiazasilepines. Tetrahedron Lett. 2005, 46, 315-317.
30. Shyamal, A.; Kale, K. S. New iron(III) complexes of tridentate ONO donor dibasic Schiff bases derived from salicylaldehyde and substituted salicylaldehyde and o-aminobenzyl alcohol. Indian J. Chem. 1980, 19A, 486-491.
31. Tasaka, M.; Hirotsu, M.; Kojima, M.; Utsuno, S.; Yoshikawa, Y. Syntheses, characterization, and molecular mechanics calculations of optically active silatrane derivatives. Inorg. Chem. 1996, 35, 6981-6986.
32. Singh, K.; Singh, R. V.; Tandon, J. P. Synth. React. Inorg. Met. - Org. Chem. 1987, 17, 385.
33. 29Si NMR of five-and six-coordinate organosilicon complexes. J. Organomet. Chem. 1980, 186, 13-17.
34. Armarego, W. L. F.; Perrin, D. D. Purification of Laboratory Chemicals, 4th Edn.; Butterworth, Heinemann: Oxford, 1997.