Automated synthesis of a library of triazolated 1,2,5-thiadiazepane 1,1-dioxides via a double aza-Michael strategy

ACS Combinatorial Science

Volumn 14, Issue 8, 2012, Pages 456-459

  Zang, Qin ^a   Javed, Salim ^a   Hill, David ^a   Ullah, Farman ^a,b   Bi, Danse ^a   Porubsky, Patrick ^a   Neuenswander, Benjamin ^a   Lushington, Gerald H ^a   Santini, Conrad ^a   Organ, Michael G ^a,b   Hanson, Paul R ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b YORK UNIVERSITY   (Canada)

Author keywords

aza Michael; parallel synthesis; triazolated 1,2,5 thiadiazepane 1,1 dioxides

Indexed keywords

1,4 DIAZEPANE; 1,4-DIAZEPANE; AZEPINE DERIVATIVE; HETEROCYCLIC COMPOUND; SULFUR;

AUTOMATION; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; LETTER; MOLECULAR LIBRARY; SYNTHESIS;

AUTOMATION; AZA COMPOUNDS; AZEPINES; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; SMALL MOLECULE LIBRARIES; SULFUR;

EID: 84865007543     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co300049u     Document Type: Review

References (30)

1. Kündig, P. The Future of Organic Synthesis Science 2006, 314, 430-431
2. Brändli, C.; Maiwald, P.; Schröer, J. Automated Equipment for High-Throughput Experimentation Chimia 2003, 57, 284-289
3. Koppitz, M.; Eis, K. Automated Medicinal Chemistry Drug Discovery Today 2006, 11, 561-568
4. Fenster, E.; Long, T.; Zang, Q.; Hill, D.; Neunswander, B.; Lushington, G.; Zhao, A.; Santini, C.; Hanson, P. R. Automated Synthesis of a 184-Member Library of Thiadiazepan-1,1-dioxide-4-ones ACS Comb. Sci. 2011, 13, 244-250
5. Carpintero, M.; Cifuentes, M.; Ferritto, R.; Haro, R.; Toledo, M. A. Automated Liquid-Liquid Extraction Workstation for Library Synthesis and Its Use in the Parallel and Chromatography-Free Synthesis of 2-Alkyl-3-alkyl-4(3 H)-quinazolinones J. Comb. Chem. 2007, 9, 818-822
6. Vickerstaffe, E.; Warrington, B. H.; Ladlow, M.; Ley, S. V. A Highly Automated, Polymer-Assisted Strategy for the Preparation of 2- Alkylthiobenzimidazoles and N, N ′-Dialkylbenzimidazolin-2-ones J. Comb. Chem. 2005, 7, 385-397
7. Weber, A.; von Roedern, E.; Stilz, H. U. SynCar: An Approach to Automated Synthesis J. Comb. Chem. 2005, 7, 178-184
8. Malik, L.; Tofteng, A. P.; Pedersen, S. L.; Søerensen, K. K.; Jensen, K. J. Automated " X - Y " Robot for Peptide Synthesis with Microwave Heating: Application to Difficult Peptide Sequences and Protein Domains J. Pept. Sci. 2010, 16, 506-512
9. Meier, M. A. R.; Hoogenboom, R.; Schubert, U. S. Combinatorial Methods, Automated Synthesis and High-Throughput Screening in Polymer Research: The Evolution Continues Macromol. Rapid Commun. 2004, 25, 21-33
10. Seeberger, P. H. Automated Oligosaccharide Synthesis Chem. Soc. Rev. 2008, 37, 19-28
11. Doi, T.; Fuse, S.; Miyamoto, S.; Nakai, K.; Sasuga, D.; Takahashi, T. A Formal Total Synthesis of Taxol Aided by an Automated Synthesizer Chem.-Asian J. 2006, 1, 370-383
12. Baxendale, I. R.; Griffiths-Jones, C. M.; Ley, S. V.; Tranmer, G. K. Preparation of the Neolignan Natural Product Grossamide by a Continuous-Flow Process Synlett. 2006, 427-430
13. Baxendale, I. R.; Deeley, J.; Griffiths-Jones, C. M.; Ley, S. V.; Saaby, S.; Tranmer, G. K. A Flow Process for the Multi-step Synthesis of the Alkaloid Natural Product Oxomaritidine: A New Paradigm for Molecular Assembly Chem. Commun. 2006, 2566-2568
14. Tanaka, Y.; Fuse, S.; Tanaka, H.; Doi, T.; Takahashi, T. An Efficient Synthesis of a Cyclic Ether Key Intermediate for 9-Membered Masked Enediyne Using an Automated Synthesizer Org. Process Res. Dev. 2009, 13, 1111-1121
15. Fuse, S.; Okada, K.; Iijima, Y.; Munakata, A.; Machida, K.; Takahashi, T.; Takagi, M.; Shin-ya, K.; Doi, T. Total Synthesis of Spiruchostatin B Aided by An Automated Synthesizer Org. Biomol. Chem. 2011, 9, 3825-3833
16. Zang, Q.; Javed, S.; Ullah, F.; Zhou, A.; Knudtson, C. A.; Bi, D.; Basha, F. Z.; Organ, M. G.; Hanson, P. R. Application of a Double aza-Michael Reaction in a "Click, Click, Cy-Click" Strategy: From Bench to Flow Synthesis 2011, 2743-2750
17. Zhou, A.; Rayabarapu, D.; Hanson, P. R. "Click, Click, Cyclize": A DOS Approach to Sultams Utilizing Vinyl Sulfonamide Linchpins Org. Lett. 2009, 11, 531-534
18. For DOS, see: (b) Burke, M. D.; Schreiber, S. L. A Planning Strategy for Diversity-oriented Synthesis Angew. Chem., Int. Ed. 2004, 43, 46-58
19. Spiegel, D. A.; Schroeder, F. C.; Duvall, J. R.; Schreiber, S. L. An Oligomer-based Approach to Skeletal Diversity in Small-molecule Synthesis J. Am. Chem. Soc. 2006, 128, 14766-14767
20. Comer, E.; Rohan, E.; Deng, L.; Porco, J. A. An Approach to Skeletal Diversity Using Functional Group Pairing of Multifunctional Scaffolds Org. Lett. 2007, 9, 2123-2126
21. Nielsen, T. E.; Schreiber, S. L. Towards the Optimal Screening Collection: A Synthesis Strategy Angew. Chem., Int. Ed. 2008, 47, 48-56
22. Drews, J. A Historical Perspective Science 2000, 287, 1960-1964
23. Navia, M. A. A Chicken in Every Pot, Thanks to Sulfonamide Drugs Science 2000, 288, 2132-2133
24. Faisal, S.; Ullah, F.; Maity, P. K.; Rolfe, A.; Samarakoon, T. B.; Porubsky, P.; Neuenswander, B.; Lushington, G. H.; Basha, F. Z.; Organ, M. G.; Hanson, P. R. Facile (Triazolyl)methylation of MACOS-derived Benzofused Sultams Utilizing ROMP-derived OTP Reagents. ACS Comb. Sci. 2012, 14, 268-272
25. Rolfe, A.; Painter, T. O.; Asad, N.; Hur, M. Y.; Jeon, K. O.; Brzozowski, M.; Klimberg, S. V.; Porubsky, P.; Neunswander, B.; Lushington, G.; Santini, C.; Hanson, P. R. Triazole-Containing Isothiazolidine 1,1-Dioxide Library Synthesis: One-Pot, Multi-Component Protocols for Small Molecular Probe Discovery. ACS Comb. Sci. 2011, 13, 511-517
26. NAr Protocol ACS Comb. Sci. 2011, 13, 653-658
27. Fenster, E.; Long, T.; Zang, Q.; Hill, D.; Neunswander, B.; Lushington, G.; Zhao, A.-H.; Santini, C.; Hanson, P. R. Automated Synthesis of a 184-Member Library of Thiadiazepan-1,1-dioxide-4-ones ACS Comb. Sci. 2011, 13, 244-250
28. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Delivery Rev. 1997, 23, 3-25
29. Cruciani, G.; Meniconi, M.; Carosati, E.; Zamora, I.; Mannhold, R. VOLSURF: A Tool for Drug ADME-Properties Prediction. In Methods and Principles in Medicinal Chemistry; van de Waterbeemd, H.; Lennernäs, H.; Artursson, P. Eds.; Wiley-VCH Verlag GmbH & Co.: Weinheim, Germany, 2003.
30. Pearlman, R. S.; Smith, K. M. Metric Validation and the Receptor-Relevant Subspace Concept J. Chem. Inf. Comput. Sci. 1999, 39, 28-35