Synthesis of an isoindoline-annulated, tricyclic sultam library via microwave-assisted, continuous-flow organic synthesis (MACOS)

Synthesis (Germany)

Volumn 44, Issue 16, 2012, Pages 2547-2554

  Ullah, Farman ^a,b   Zang, Qin ^b   Javed, Salim ^b   Porubsky, Patrick ^b   Neuenswander, Benjamin ^b   Lushington, Gerald H ^b   Hanson, Paul R ^b   Organ, Michael G ^a,b  

^a YORK UNIVERSITY   (Canada)

^b UNIVERSITY OF KANSAS   (United States)

Author keywords

aza Michael addition; continuous flow; Heck reaction; isoindolines; MACOS; sultams

Indexed keywords

AZA-MICHAEL ADDITION; CONTINUOUS FLOWS; HECK REACTIONS; ISOINDOLINES; MACOS; SULTAMS;

SULFUR COMPOUNDS;

ADDITION REACTIONS;

3 (3,4 DIMETHOXYPHENETHYL) 3,4,6,10B TETRAHYDRO 1H [1,2,4]THIADIAZINO[5,4 A]ISOINDOLE 4(3H)ONE 2,2 DIOXIDE; 3 (4 CHLOROBENZYL) 6,10B DIHYDRO 1H [1,2,4]THIADIAZINO[5,4 A]ISOINDOL 4(3H)ONE 2,2 DIOXIDE; 3 (CYCLOHEXYLMETHYL) 8 FLUORO 3,4,6,10B TETRAHYDRO 1H [1,2,4]THIADIAZINO[5,4 A]ISOINDOLE 4(3H)ONE 2,2 DIOXIDE; 3 CYCLOHEXYL 8 FLUORO 6,10B DIHYDRO 1H [1,2,4]THIADIAZINO[5,4 A]ISOINDOL 4(3H)ONE 2,2 DIOXIDE; 3 CYCLOHEXYL 9 METHYL 3,4,6,10B TETRAHYDRO 1H [1,2,4]THIADIAZINO[5,4 A]ISOINDOLE 4(3H)ONE 2,2 DIOXIDE; 3 CYCLOHEXYL 9 METHYL 6,10B DIHYDRO 1H [1,2,4]THIADIAZINO[5,4 A]ISOINDOL 4(3H)ONE 2,2 DIOXIDE; 3 DECYL 6,10B DIHYDRO 1H [1,2,4]THIADIAZINO[5,4 A]ISOINDOL 4(3H)ONE 2,2 DIOXIDE; 7 (3,4 DIMETHOXYPHENETHYL) 4B,7,8,10 TETRAHYDRO 5H [1,3]DIOXOLO[4,5F][1,2,4]THIADIAZINO[5,4 A]ISOINDOLE 6,6 DIOXIDE; ISOINDOLE DERIVATIVE; TRIBACTAM; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; DEPROTECTION REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; MICROWAVE ASSISTED CONTINUOUS FLOW ORGANIC SYNTHESIS; MICROWAVE COOKING; ONE POT SYNTHESIS;

EID: 84864866570     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1289791     Document Type: Article

References (37)

1. Tierney PJ, Lidstrom P. Microwave Assisted Organic Synthesis. Blackwell Publishing Oxford: 2005
2. Kappe CO. Angew. Chem. Int. Ed.: 2004; 43 6250
3. Jähnisch K, Hessel V, Löwe H, Baerns M. Angew. Chem. Int. Ed.: 2004; 43 406
4. Pennemann H, Watts P, Haswell SJ, Hessel V, Lowe H. Org. Process Res. Dev.: 2004; 8 422
5. Bremner S, Organ MG. J. Comb. Chem.: 2007; 9 14
6. Comer E, Organ MG. J. Am. Chem. Soc.: 2005; 127 8160
7. Organ MG, Comer E. Chem.-Eur. J.: 2005; 11 7223
8. Bagley MC, Jenkins RL, Lubinu MC, Mason C, Wood R. J. Org. Chem.: 2005; 70 7003
9. Saaby S, Baxendale IR, Ley SV. Org. Biomol. Chem.: 2005; 3 3365
10. He P, Haswell SJ, Fletcher PD.I. Appl. Catal., A: 2004; 274 111
11. Cablewski T, Faux AF, Strauss CR. J. Org. Chem.: 1994; 59 3408
12. Shore G, Yoo W.-J, Li C.-J, Organ MG. Chem.-Eur. J.: 2010; 16 126
13. Shore G, Organ MG. Chem. Commun.: 2008; 838
14. Shore G, Organ MG. Chem.-Eur. J.: 2008; 14 9641
15. Shore G, Morin S, Mallik D, Organ MG. Chem.-Eur. J.: 2008; 14 1351
16. Shore G, Morin S, Organ MG. Angew. Chem. Int. Ed.: 2006; 45 2761
17. Organ MG, Hanson PR, Rolfe A, Samarakoon TB, Ullah F. J. Flow Chem.: 2011; 1 32
18. Zang Q, Javed S, Ullah F, Zhou A, Knudtson CA, Bi D, Basha FZ, Organ MG, Hanson PR. Synthesis: 2011; 2743
19. Ullah F, Samarakoon TB, Rolfe A, Kurtz RD, Hanson PR, Organ MG. Chem.-Eur. J.: 2010; 16 10959
20. Moseley JD. Org. Process Res. Dev.: 2008; 12 967
21. Styring P, Parracho AI. R. Beilstein J. Org. Chem.: 2009; 5 29
22. Rolfe A, Ullah F, Samarakoon TB, Kurtz RD, Porubsky P, Neunswander B, Lushington G, Santini C, Organ MG, Hanson PR. ACS Comb. Sci.: 2011; 13 653
23. Drews J. Science (Washington, D.C.): 2000; 287 1960
24. Scozzafava A, Owa T, Mastrolorenzo A, Supuran CT. Curr. Med. Chem.: 2003; 10 925
25. Lebegue N, Gallet S, Flouquet N, Carato P, Pfeiffer B, Renard P, Léonce S, Pierré A, Chavatte P, Berthelot P. J. Med. Chem.: 2005; 48 7363
26. Silvestri R, Marfè G, Artico M, La Regina G, Lavecchia A, Novellino E, Morgante M, Di Stefano C, Catalano G, Filomeni G, Abruzzese E, Ciriolo MR, Russo MA, Amadori S, Cirilli R, La Torre F, Salimei PS. J. Med. Chem.: 2006; 49 5840
27. Tan DS. Nat. Chem. Biol.: 2005; 1 74
28. Thomas GL, Spandl RJ, Glansdorp FG, Welch M, Bender A, Cockfield J, Lindsay JA, Bryant C, Brown DF. J, Loiseleur O, Rudyk H, Ladlow M, Spring DR. Angew. Chem. Int. Ed.: 2008; 47 2808
29. Spandl RJ, Diaz-Gavilan M, O'Connell KM. G, Thomas GL, Spring DR. Chem. Rec.: 2008; 8 129
30. Shaw JT. Nat. Prod. Rep.: 2009; 26 11
31. Thomas GL, Wyatt EE, Spring DR. Curr. Opin. Drug Discovery Dev.: 2006; 9 700
32. Samarakoon TB, Hur MY, Kurtz RD, Hanson PR. Org. Lett.: 2010; 12 2182
33. Rolfe A, Samarakoon TB, Hanson PR. Org. Lett.: 2010; 12 1216
34. Mazik M, Kuschel M. Eur. J. Org. Chem.: 2008; 1517
35. Julian LD, Hartwig JF. J. Am. Chem. Soc.: 2010; 132 13813
36. Routier S, Saugé L, Ayerbe N, Coudert G, Mérour J. Tetrahedron Lett.: 2002; 43 589
37. El Kazzouli S, Koubachi J, Berteina-Raboin S, Mouaddib A, Guillaumet G. Tetrahedron Lett.: 2006; 47 8575