Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2009 - Issue 2
244
Views
10
CrossRef citations to date
0
Altmetric
Original Articles

Unexpected and Green Synthesis of Azapodophyllotoxin Derivatives via Microwave-Assisted Multicomponent Reactions in Ammonia Water

, , , , &
Pages 235-241 | Received 22 Dec 2008, Published online: 29 Dec 2009

REFERENCES

  • (a) Matlack , A. S. Introduction to Green Chemistry ; Marcel Dekker Inc. : New York , 2001 ; (b) Dallinger , D. ; Kappe , C. O. Microwave-assisted synthesis in water as solvent. Chem. Rev. 2007, 107, 2563–2591 .
  • (a) Lindstrom , U. M. Stereoselective organic reactions in water . Chem. Rev. 2002 , 102 , 2751 – 2772 ; (b) Li , C. J. Organic reactions in aqueous media with a focus on carbon–carbon bond formations: A decade update . Chem. Rev. 2005 , 105 , 3095 – 3165 ; (c) Pirrung , M. C. Acceleration of organic reactions through aqueous solvent effects . Chem. Eur. J. 2006 , 12 , 1312 – 1317 ; (d) Strauss , C. R. Microwave-assisted reactions in organic synthesis—Are there any nonthermal microwave effects? Comments . Angew. Chem., Int. Ed. 2002 , 41 , 3589 – 3590 ; (e) Kappe , C. O. Synthetic methods: Controlled microwave heating in modern organic synthesis . Angew. Chem., Int. Ed. 2004 , 43 , 6250 – 6284 .
  • Strauss , C. R. ; Trainor , R. W. Developments in microwave-assisted organic chemistry . Aust. J. Chem. 1995 , 48 , 1665 – 1692 .
  • (a) Ramon , D. J. ; Miguel , Y. Asymmetric multicomponent reactions (AMCRs): The new frontier . Angew. Chem., Int. Ed. 2005 , 44 , 1602 – 1634 ; (b) Orru , R. V. A. ; de Greef , M. Recent advances in solution-phase multicomponent methodology for the synthesis of heterocyclic compounds . Synthesis 2003 , 1471 – 1499 ; (c) Weber , L. ; Illgen , K. ; Almstetter , M. Discovery of new multicomponent reactions with combinatorial methods . Synlett 1999 , 366 – 374 .
  • (a) Magedov , I. V. ; Manpadi , M. ; Van Slambrouck , S. ; Steelant , W. F. A. ; Rozhkova , E. ; Przheval'skii , N. M. ; Rogelj , S. ; Kornienko , A. Discovery and investigation of antiproliferative and apoptosis-inducing properties of new heterocyclic podophyllotoxin analogues accessible by a one-step multicomponent synthesis. J. Med. Chem. 2007, 50, 5183–5192; (b) Hitotsuyanagi , Y. ; Fukuyo , M. ; Tsuda , K. ; Kobayashi , M. ; Ozeki , A. ; Itokawa , H. ; Takeya , K. 4-Aza-2,3-dehydro-4-deoxypodophyllotoxins: Simple Aza-podophyllotoxin analogues possessing potent cytotoxicity. Bioorg. Med. Chem. 2000, 10, 315–317.
  • Skrastins , I. ; Vitolina , R. ; Kastron , V. V. ; Dubur , G. Y. Synthesis and cardiotonic activity of furo[3,4-b]- and difuro[3,4-b:3,4-e]pyridines . Khim.-Farm. Zh. 1995 , 29 , 31 – 33 .
  • Skrastins , I. ; Kastron , V. ; Vitolins , R. ; Duburs , G. ; Stivrina , M. S. ; Kaidaka , K. Synthesis and pharmacological activity of furo-1,4-dihydropyridines . Khim.-Farm. Zh. 1989 , 23 , 1323 – 1326 .
  • Velten , R. ; Adelt , I. ; Boehmer , J. ; Frackenpohl , J. ; Schenke , T. ; Loesel , P. ; Malsam , O. ; Arnold , C. Preparation of fused quinolines as pesticides . WO Patent 2005097802, 2005; Chem. Abstr. 2005 , 143 , 405891 .
  • Carroll , W. A. ; Agrios , K. A. ; Basha , F. Z. ; Chen , Y. ; Kort , M. E. ; Kym , P. R. ; Tang , R. ; Turner , S. C. ; Yi , L. Preparation of tricyclic heterocycles as potassium channel openers . WO Patent 2000024741, 2000; Chem. Abstr. 2000 , 132 , 308329 .
  • Patmore , L. ; Duncan , G. P. ; Clarke , B. ; Anderson , A. J. ; Greenhouse , R. ; Pfister , J. R. RS 30026: A potent and effective calcium channel agonist . Brit. J. Pharmacol. 1990 , 99 , 687 – 694 .
  • (a) Tomioka , K. ; Kubota , Y. ; Koga , K. Design, synthesis, and antitumor activity-absolute configuration relationships of podophyllotoxin aza-analogs . Tetrahedron 1993 , 49 , 1891 – 1900 ; (b) Lienard , P. ; Quirion , J. C. ; Husson , H. P. Asymmetric synthesis, XXVIII: Hydroxylated benzoquinolizidine analogs of podophyllotoxin via the CN(R,S) method . Tetrahedron 1993 , 49 , 3995 – 4006 ; (c) Madalengoitia , J. S. ; Macdonald , T. L. Synthesis of tetrahydrofurocarbazolones via intramolecular Diels–Alder reactions . Tetrahedron Lett. 1993 , 34 , 6237 – 6240 ; (d) Lehnert , E. K. ; Miller , K. E. ; Madalengoitia , J. S. ; Guzi , T. J. ; Macdonald , T. L. DNA topoisomerase II inhibition by substituted 1,2,3,4-tetrahydro-carboline derivatives . Bioorg. Med. Chem. Lett. 1994 , 4 , 2411 – 2416 ; (e) Hitotsuyanagi , Y. ; Fukuyo , M. ; Tsuda , K. ; Kobayashi , M. ; Ozeki , A. ; Itokawa , H. ; Takeya , K. 4-Aza-2,3-dehydro-4-deoxypodophyllotoxins: Simple Aza-podophyllotoxin analogues possessing potent cytotoxicity . Bioorg. Med. Chem. Lett. 2000 , 10 , 315 – 317 ; (f) Tratrat , C. ; Giorgi-Renault , S. ; Husson , H. P. A multicomponent reaction for the one-pot synthesis of 4-aza-2,3-didehydropodophyllotoxin and derivatives . Org. Lett. 2002 , 4 , 3187 – 3189 .
  • (a) Tu , S. ; Zhang , Y. ; Jia , R. ; Jiang , B. ; Zhang , J. ; Ji , S. A multi-component reaction for the synthesis of N-substituted furo[3,4-b]quinoline derivatives under microwave irradiation . Tetrahedron Lett. 2006 , 47 , 6521 – 6525 ; (b) Tu , S. ; Zhang , Y. ; Zhang , J. ; Jiang , B. ; Jia , R. ; Zhang , J. ; Ji , S. A simple procedure for the synthesis of 4-Aza-podophyllotoxin derivatives in water under microwave irradiation conditions . Synlett 2006 , 17 , 2785 – 2790 .
  • (a) Shi , F. ; Wang , Q. ; Tu , S. ; Zhou , J. ; Jiang , B. ; Li , C. ; Zhou , D. ; Shao , Q. ; Cao , L. A green and efficient synthesis of furo[3,4-e]pyrazolo[3,4-b]pyridine derivatives in water under microwave irradiation without catalyst . J. Heterocycl. Chem. 2008 , 45 , 1103 – 1108 ; (b) Shi , F. ; Zhou , D. ; Tu , S. ; Shao , Q. ; Li , C. ; Cao , L. An efficient microwave-assisted synthesis furo[3,4-b][4,7]phenanthroline and indeno[2,1-b][4,7]phenanthroline derivatives in water . J. Heterocycl. Chem. 2008 , 45 , 1065 – 1070 ; (c) Shi , F. ; Zhou , D. ; Li , C. ; Shao , Q. ; Cao , L. ; Tu , S. An efficient and facile microwave-assisted synthesis of benzo[b][4,7]phenanthroline derivatives in water . J. Heterocycl. Chem. 2008 , 45 , 405 – 410 .
  • Tu , S. ; Lu , Z. ; Shi , D. ; Yao , C. ; Gao , Y. ; Guo , C. A convenient synthesis of 9-aryl-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-diones under microwave irradiation without solvent . Synth. Commun. 2002 , 32 , 2181 – 2185 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.