Synthesis of (±)-8-oxa-3-azabicyclo[32.1]octan-2-thione and (±)-2-oxa-5-azabicyclo[2.2.1]heptan-6-thione: Potential synthons for the preparation of novel heteroaryl-annulated bicyclic morpholines

Synthesis

Volumn , Issue 7, 2011, Pages 1113-1119

  Walker, Daniel P ^a   Wishka, Donn G ^a   Beagley, Paul ^a   Turner, Gemma ^a   Solesbury, Nicola ^a  

^a PFIZER INC   (United States)

Author keywords

bicyclic compounds; furans; heterocycles; hydrogenation; stereoselective synthesis

Indexed keywords

BICYCLIC COMPOUNDS; FURAN DERIVATIVES; FURANS; HETEROCYCLES; MORPHOLINES; STEREOSELECTIVE SYNTHESIS; SYNTHONS; TETRA-HYDROFURAN;

AROMATIC COMPOUNDS; HYDROGENATION; ORGANIC POLLUTANTS;

STEREOSELECTIVITY;

2 OXA 5 AZABICYCLO[2.2.1]HEPTAN 6 ONE; 2 OXA 5 AZABICYCLO[2.2.1]HEPTAN 6 THIONE; 4 (4 METHYLPHENYLSULFONAMIDO)TETRAHYDROFURAN 2 CARBOXYLIC ACID; 4 AMINOTETRAHYDRO 2 FURANCARBOXYLIC ACID; 8 OXA 3 AZABICYCLO[3.2.1]OCTAN 2 THIONE; AGN 193080; BICYCLIC MORPHOLINE DERIVATIVE; BLI 489; FINAFLOXACIN; FURAN DERIVATIVE; GEFITINIB; LINEZOLID; METHYL 4 (4 METHYLPHENYLSULFONAMIDO)TETRAHYDROFURAN 2 CARBOXYLIC ACID; METHYL 4 (TERT BUTOXYCARBONYLAMINO)TETRAHYDROFURAN 2 CARBOXYLIC ACID; METHYL 4 AMINOTETRAHYDROFURAN 2 CARBOXYLIC ACID; METHYL 5 [(TERT BUTOXYCARBONYLAMINO)METHYL]TETRAHYDROFURAN 2 CARBOXYLIC ACID; MORPHOLINE DERIVATIVE; N TOSYL 2 OXA 5 AZABICYCLO[2.2.1]HEPTAN 6 ONE; REBOXETINE; THIOKETONE; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGENATION; STEREOCHEMISTRY;

EID: 79953026294     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258464     Document Type: Article

References (35)

1. Brickner S J., Barbachyn M R., Hutchinson D K., Manninen P R., J. Med. Chem. 2008 51 1981
2. Barker A J., Gibson K H., Grundy W, Godfrey A A., Barlow J J., Healy M P., Woodburn J R., Ashton S E., Curry B J., Scarlett L, Henthorn L, Richards L, Bioorg. Med. Chem. Lett. 2001 1911
3. Kasper S, El Giamal N, Hilger E, Exp. Opin. Pharmacother. 2000 1 771
4. Abe T, Matsunaga H, Mihira A, Sato C, Ushirogochi H, Sato K, Takasaki T, Venkatesan A M., Mansour T S., Patent Cooperation Treaty WO 2003/093277 2003; Chem. Abstr. 2003, 139, 381300, Tabei K, Feng X, Venkatesan A M., Abe T, Hideki U, Mansour T S., Siegel M M., J. Med. Chem. 2004 47 3674
5. Petersen P J., Jones C H., Venkatesan A M., Bradford P A., Antimicrob. Agents Chemother. 2009 53 1698
6. Vasiliou S, Vicente M, Castaner R, Drugs Future 2009 34 451
7. Munk S A., Harcourt D, Ambrus G, Denys L, Gluchowski C, Burke J A., Kharlamb A B., Manlapaz C A., Padillo E U., Runde E, Williams L, Wheeler L A., Garst M E., J. Med. Chem. 1996 39 3533
8. Griffin R J., Fontana G, Golding B T., Guiard S, Hardcastle I R., Leahy J J. J., Martin N, Richardson C, Rigoreau L, Stockley M, Smith G C. M., J. Med. Chem. 2005 48 569
9. Blizzard T B., DiNinno F, Morgan J D. II., Chen H Y., Wu J Y., Gude C, Kim S, Chan W, Birzin E T., Yang Y T., Pai L.-Y, Zhang Z, Hayes E C., DaSilva C A., Tang W, Rohrer S P., Schaeffer J M., Hammond M L., Bioorg. Med. Chem. Lett. 2004 3861
10. Roecker A J., Coleman P J., Mercer S P., Schreier S D., Buser C A., Walsh E S., Hamilton K, Lobell R B., Tao W, Diehl R E., South V J., Davide J P., Kohl N E., Yan Y, Kuo L C., Li C, Fernandez-Metzler C, Mahan E A., Prueksaritanont T, Hartman G D., Bioorg. Med. Chem. Lett. 2007 5677
11. Venkatesan A M., Chen Z, Santos O D., Dehnhardt C, Santos E D., Ayral-Kaloustian S, Mallon R, Hollander I, Feldberg L, Lucas J, Yu K, Chaudhary I, Mansour T S., Bioorg. Med. Chem. Lett. 2010 5869
12. Zask A, Kaplan J, Verheijen J C., Richard D J., Curran K, Brooijmans N, Bennett E M., Toral-Barza L, Hollander I, Ayral-Kaloustian S, Yu K, J. Med. Chem. 2009 52 7942
13. Jagodzinski T S., Chem. Rev. 2003 103 197
14. Bromidge S M., Arban R, Bertani B, Bison S, Borriello M, Cavanni P, Dal Forno G, Di-Fabio R, Donati D, Fontana S, Gianotti M, Gordon L J., Granci E, Leslie C P., Moccia L, Pasquarello A, Sortori I, Sava A, Watson J M., Worby A, Zonzini L, Zucchelli V, J. Med. Chem. 2010 53 5827
15. Thurkauf A, Chen X, Zhang S, Gao Y, Kieltyka A, Wasley J W. F., Brodbeck R, Greenlee W, Ganguly A, Zhao H, Bioorg. Med. Chem. Lett. 2003 2921
16. Weber M, Jager W, Erker T, J. Heterocycl. Chem. 2003 40 851
17. Moore J A., Partain E M. III, J. Polym. Sci. Polym. Lett. Ed. 1975 13 333
18. See:, Moore J A., Kelly J E., Org. Prep. Proced. Int. 1972 4 289
19. Moore J A., Kelly J E., Org. Prep. Proced. Int. 1974 6 255
20. Bradshaw J S., Baxter S L., Lamb J D., Izatt R M., Christensen J J., J. Am. Chem. Soc. 1981 103 1821
21. Allen R D., Tran H W., Aust. J. Chem. 1984 34 1123
22. Ichihara A, Yamanaka T, Matsumoto T, Bull. Chem. Soc. Jpn. 1965 38 1165
23. Matsumoto T, Ichihara A, Bull. Chem. Soc. Jpn. 1960 33 1015
24. Wolter F E., Schneider K, Davies B P., Socher E R., Nicholson G, Seitz O, Sussmuth R D., Org. Lett. 2009 11 2804
25. Lee G C. M., Holmes J M., Harcourt D A., Garst M E., J. Org. Chem. 1992 57 3126
26. Bergmeier S C., Cobas A A., Rapoport H, J. Org. Chem. 1993 58 2369
27. Nagashima H, Ozaki N, Washiyama M, Itoh K, Tetrahedron Lett. 1985 26 657
28. Ji S, Gortler L B., Waring A, Battisti A, Bank S, Closson W D., J. Am. Chem. Soc. 1967 89 5311
29. Milne H B., Peng C.-H, J. Am. Chem. Soc. 1957 79 639
30. A related heterocycle, isoquinuclidinone, has been prepared via thermal cyclization of cis -4-aminocyclohexane-carboxylic acid in Dowtherm A, see:, Pearlman W M., Org. Syn. 1969 49 75
31. Chung J Y. L., Ho G.-J, Synth. Commun. 2002 32 1985
32. See:, Werner L H., Ricca S Jr., J. Am. Chem. Soc. 1958 80 2733
33. Casabona D, Cativiela C, Tetrahedron 2006 62 10000
34. Gong L, Hogg J H., Collier J, Wilhelm R S., Soderberg C, Bioorg. Med. Chem. Lett. 2003 3597
35. DCC has been used to effect lactamization on a related carbocyclic system, see:, Grunewald G L., Sall D J., Monn J A., J. Med. Chem. 1988 31 433