An expedient and practical approach to functionalized 3-aza-, 3-oxa-, and 3-thiabicyclo[33.1]nonane systems

Synthesis (Germany)

Volumn 46, Issue 9, 2014, Pages

  Ishchenko, Aleksandr Yu ^a,b   Yanik, Stanislav ^a   Rusanov, Eduard B ^c   Komarov, Igor V ^a   Kirby, Anthony J ^d  

^a TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

^b ENAMINE LTD   (Ukraine)

^c INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

^d UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

annulation; bicyclic compounds; Caglioti reaction; diversity oriented synthesis; medicinal chemistry

Indexed keywords

SCAFFOLDS;

ANNULATION; BICYCLIC COMPOUNDS; CAGLIOTI REACTION; DIVERSITY-ORIENTED SYNTHESIS; MEDICINAL CHEMISTRY;

SYNTHESIS (CHEMICAL);

7 BENZYL 3 TERT BUTYL 7 ENDO 3 AZABICYCLO[3.3.1]NONANE 3,7 DICARBOXYLIC ACID; 7 ENDO (9 AMINO 3 OXABICYCLO[3.3.1]NON 7 YL)CARBAMIC ACID TERT BUTYL ESTER; 7 ENDO (9 AMINO 3,3 DIOXO 3 THIABICYCLO[3.3.1]NON 7 YL)CARBAMIC ACID TERT BUTYL ESTER; 7 ENDO 1 (7 BENZYLOXYCARBONYL 3 HIABICYCLO[3.3.1]NON 9 YLIDENE)PYRROLIDINIUM BROMIDE; 7 ENDO 1 (7 BENZYLOXYCARBONYL 3 OXABICYCLO[3.3.1]NON 9 YLIDENE)PYRROLIDINIUM BROMIDE; 7 ENDO 1 (7 BENZYLOXYCARBONYL 3 TERT BUTOXYCARBONYL 3 AZABICYCLO[3.3.1]NON 9 YLIDENE)PYRROLIDINIUM BROMIDE; 7 ENDO 1 (7 BENZYLOXYCARBONYL 3 THIABICYCLO[3.3.1]NON 9 YLIDENE)PYRROLIDINIUM BROMIDE; 7 ENDO 3 (TERT BUTOXYCARBONYL) 3 AZABICYCLO[3.3.1]NONANE 7 CARBOXYLIC ACID; 7 ENDO 3 AZABICYCLO[3.3.1]NONANE 7 CARBOXYLIC ACID; 7 ENDO 7 [[(TERT BUTYLOXY)CARBONYL]AMINO] 9 OXO 3 OXABICYCLO[3.3.1]NONANE; 7 ENDO 9 OXO 3 AZABICYCLO[3.3.1]NONANE 3,7 DICARBOXYLIC ACID 7 BENZYL ESTER 3 TERT BUTYL ESTER; 7 ENDO 9 OXO 3 OXABICYCLO[3.3.1]NONANE 7 CARBOXYLIC ACID BENZYL ESTER; 7 ENDO 9 OXO 3 THIABICYCLO[3.3.1]NONANE 7 CARBOXYLIC ACID 3,3 DIOXIDE; 7 ENDO 9 OXO 3 THIABICYCLO[3.3.1]NONANE 7 CARBOXYLIC ACID BENZYL ESTER; 7 EXO 3 (TERT BUTOXYCARBONYL) 3 AZABICYCLO[3.3.1]NONANE 7 CARBOXYLIC ACID; 7 EXO 3 AZABICYCLO[3.3.1]NONANE 7 CARBOXYLIC ACID HYDROCHLORIDE; BENZYL 7' ENDO SPIRO(1,3 DIOXANE 2,9' [3]THIABICYCLO[3.3.1]NONANE) 7' CARBOXYLIC ACID; BENZYL 7' ENSO SPIRO(1,3 DIOXANE 2,9' [3]THIABICYCLO[3.3.1]NONANE) 7' CARBOXYLATE 3',3' DIOXIDE; BICYCLO[3.3.1]NONANE DERIVATIVE; TERT BUTYL 7 ENDO (3,3 DIOXIDO 9 OXO 3 THIABICYCLO[3.3.1]NON 7 YL)CARBAMIC ACID; TERT BUTYL 7 ENDO 7 (BENZYLOXYCARBONYL) 9 (HYDROXYIMINO) 3 AZABICYCLO[3.3.1]NONANE 3 CARBOXYLIC ACID; TERT BUTYL 7 ENDO 7 [[(BENZYLOXY)CARBONYL]AMINO] 9 OXO 3 AZABICYCLO[3.3.1]NONANE 3 CARBOXYLIC ACID; TERT BUTYL 7 ENDO 9 (HYDROXYIMINO) 3 OXABICYCLO[3.3.1]NONAN 7 YL CARBAMIC ACID; TERT BUTYL 7 ENDO 9 (HYDROXYIMINO) 3,3 DIOXIDO 3 THIABICYCLO[3.3.1]NONAN 7 YL CARBAMIC ACID; TERT BUTYL 7 ENDO 9 AMINO 7 [[(BENZYLOXY)CARBONYL]AMINO]3 AZABICYCLO[3.3.1]NONANE 3 CARBOXYLIC ACID; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CAGLIOTI REACTION; CATALYST; CHEMICAL REACTION; DRUG DESIGN; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; EPIMERIZATION; PROCESS OPTIMIZATION;

EID: 84910135899     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0034-1379456     Document Type: Article

References (22)

1. Lovering F., Bikker J., Humblet C. J. Med. Chem.: 2009; 52 6752
2. Ruiz M., López-Alvarado P., Giorgi G., Menéndez J. C. Chem. Soc. Rev.: 2011; 40 3445
3. Grygorenko O. O., Radchenko D. S., Volochnyuk D. M., Tolmachev A. A., Komarov I. V. Chem. Rev.: 2011; 111 5506
4. Burkhard J. A., Wagner B., Fischer H., Schuler F., Müller K., Carreira E. M. Angew. Chem. Int. Ed.: 2010; 49 3524
5. Trabocchi A., Scarpi D., Guarna A. Amino Acids: 2008; 34 1
6. Horton D. A., Bourne G. T., Smythe M. L. Chem. Rev.: 2003; 103 893
7. Burke M. D., Schreiber S. L. Angew. Chem. Int. Ed.: 2004; 43 46
8. Spring D. R. Org. Biomol. Chem.: 2003; 1 3867
9. Nelson R. P., Lawton R. G. J. Am. Chem. Soc.: 1966; 88 2884
10. Nelson R. P., McEuten J. M., Lawton R. G. J. Org. Chem.: 1969; 34 1225
11. McEuten J. M., Nelson R. P., Lawton R. G. J. Org. Chem.: 1970; 35 690
12. Dekkers A. W. J. D, Speckamp W. N., Huisman H. O. Tetrahedron Lett.: 1971; 489
13. Stetter H., Reinartz W. Chem. Ber.: 1972; 105 2773
14. Mazurov A. A., Kombo D. C., Akireddy S., Murthy S., Hauser T. A., Jordan K. G., Gatto G. J., Yohannes D. Bioorg. Med. Chem. Lett.: 2013; 23 3927
15. Yeh V. S. C, Kurukulasuriya R., Madar D., Patel J. R., Fung S., Monzon K., Chiou W., Wang J., Jacobson P., Sham H. L., Link J. T. Bioorg. Med. Chem. Lett.: 2006; 16 5408
16. Yu J., Liu H., Xia G., Liu L., Xu Zh, Chen Q., Ma C., Sun X., Xu J., Li H., Li P., Shi Y., Xiong B., Liu X., Shen J. ACS Med. Chem. Lett.: 2012; 3 793
17. Meeuwissen H. J., van der Knaap T. A., Bickelhaupt F. Phosphorus Sulfur: 1983; 18 109
18. Meeuwissen H. J., van der Knaap T. A., Bickelhaupt F. Tetrahedron: 1983; 39 4225
19. Peters J. A., van der Toorn J. M., van Bekkum H. Tetrahedron: 1974; 30 633
20. Renzoni G. E., Borden W. T. J. Org. Chem.: 1983; 48 5231
21. Hutchins R. O., Hutchins M. K. In Comprehensive Organic Synthesis. Vol. 8 Trost B. M., Fleming I. Pergamon Press Oxford: 1991; 343 362
22. Lane C. F. Synthesis: 1975; 135