New Functionalized Derivatives of Sulfur- and Oxygen-Containing Hexacyclic Cage Compounds

• Autorzy: Romański, J. , Marchand, A.
• Języki publikacji: EN

Abstrakty

EN

Several new sulfur- and oxygen-bridged hexacyclic cage compounds have been obtained via transannular cyclization of pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione (1). Thus, cage-annulated thiapodands 9 and 10 were prepared via reaction of ditosylate 6 with 2-mercaptoethylamine (7) or 2-mercaptoethanol (8), respectively. Other ditosylate 11 was reacted with thiourea to afford the corresponding dimercapto podand 12. An optically active podand (R,R)-14 was prepared in similar fashion by reacting ditosylate 6 with (R)-2-amino-1-butanol (R)-(13). Functionalized 4-thiahexacyclo[ 5.4.1.0.02,6.03,10 .05,9.08,11]dodecanes 17a-band18a-b were prepared via reactions of 1 with 2-chloro- (15) or 2-bromoethanol (16), respectively in the presence of H2S(g) and HCl(g). The corresponding reaction of 1 with 2 equivalents of 8 produced the corresponding bisthioacetal 20, which subsequently was changed into a spiro-cage-annulated dithiacrown ether 22.

Słowa kluczowe

EN

cage systems; sulfur heterocycles; synthetic methods; crown derivatives

• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2004
• Tom: Vol. 78 / nr 2
• Strony: 223-230
• Opis fizyczny: Bibliogr. 10 poz., rys.

Twórcy

autor

Romański, J.

• University of Łódź, Section of Heteroorganic Compounds, Narutowicza 68, PL 90-136 Łódź, Poland,

autor

Marchand, A.

• University of North Texas, Department of Chemistry, Denton, Texas 76203-5070, USA ,

Bibliografia

• 1. Cookson R.C., Crundwell E. and Hudec J., Chem. Ind. (London), 1003 (1958).
• 2. CooksonR.C., Crundwell E., Hill R.R. and Hudec J., J. Chem. Soc., 3062 (1964); Marchand A.P., in: Thummel R.P., (Ed.) Advances in Theoretically Interesting Molecules, JAI: Greenwich, CT, Vol. 1, 1989, pp. 357-399; Mehta G., Srikrishna A., Veera Reddy A. and Nair Mangalam S., Tetrahedron, 37, 4543(1981).
• 3. Sasaki T., Eguchi S., Kiriyama T. and Hiroaki O., Tetrahedron, 30,2707 (1974); Marchand A.R, Amey B.E. Jr., Dave RR. and Satyanarayana N., J. Org. Chem., S3, 8644 (1988); Marchand A.R, Keith J.M., Alihodzic S., Ganguly B., Somers A.W., Hariprakasha H.K., Power T.D., Watson W.H. and Bodige S.G., Struct. Chem., 12,313(2001).
• 4. Watson W.H., Marchand A.P. and Dave P.R., Acta Cryst., Sect. C: Cryst. Struct. Commun., C43, 1569 (1987); Bott S.G., Marchand A.P., Kumar K.A., Vidyanand D., Xing D., Watson W.H., Kashyap R.P. and Sachleben R., J. Chem. Crystallogr., 25, 633 (1995).
• 5. Romański J. and Mloston G., Synthesis, 1355 (2002); see also: Romanski J., Mlostoń G. and Szynkiewicz S., Synthesis, 2259 (2003).
• 6. Liebenberg W., Van der Walt J.J. and Van der Schyf C.J., Pharmazie, 55,833 (2000) and references cited therein.
• 7. Marchand A.P., Kumar K.A., McKim A.S., MlinariC-Majerski K. and Kragol G., Tetrahedron, 53,3467 (1997).
• 8. Marchand A.P., Chong H.-S. and Alihodzic S., Tetrahedron, 55, 9687 (1999).
• 9. For a review, see Marchand A.P., Kumar K.A., McKim A.S., Alihodzic S., Chong H.-S., Krishnudu K, Takhi M., Mlinaric-Majerski K., Kragol G. and Sumanovac T., Kem. Ind., 50, 129 (2001).
• 10. The synthesis and X-ray crystal structure of a closely analogous spiro-cage-annulated crown ether has been reported; see: Watson W.H., Bodige S.G., Marchand A.P. and Chong H.-S., Struct. Chem., 11,257 (2000).