One-Step Method for the Synthesis of Nitroisoindoles via 1,3-Dipolar Cyclo­addition of Azomethine Ylides to Polynitrobenzenes

Abstract

A new one-step method for the synthesis of nitroiso­indoles was developed on the basis of 1,3-dipolar cycloadditions of unstabilized N-alkyl azomethine ylides with di- and trinitrobenzenes.

Key words

isoindoles - 1,3-dipolar cycloaddition - nitroarenes - azomethine ylides - heterocycles

• References

• 1a Rice ML, Grogan CH, Reid EE. J. Am. Chem. Soc. 1953; 75: 4911
• 1b Jaunin R. CH 612670, 1979
• 1c Jaunin R. CH 610304, 1979
• 1d Meyer MD, Altenbach RJ, Basha FZ, Carroll WA, Condon S, Elmore SW, Kerwin JF, Sippy KB, Tietje K, Wendt MD, Hancock AA, Brune ME, Buckner SA, Drizin I. J. Med. Chem. 2000; 43: 1586
• 2 For example, see: Wittig G, Tenhaeff H, Schoeh W, Koenig G. Justus Liebigs Ann. Chem. 1951; 572: 1
• 3a König K.-H, Zeeh B. Chem. Ber. 1970; 103: 2052
• 3b Zeeh B, König K.-H. Synthesis 1972; 45
• 3c Cignarella G, Savelli F, Sanna P. Synthesis 1975; 252
• 4a Anderson PS, Christy ME, Colton CD, Halczenko V, Ponticello GS, Shepard KL. J. Org. Chem. 1979; 44: 1519
• 4b Dobeneck H, Reinhard H, Deubel H, Wolkenstein D. Chem. Ber. 1969; 102: 1357
• 4c Garmaise DL, Ryan A. J. Heterocycl. Chem. 1970; 7: 413
• 4d Messerschmitt T, Von Specht H, Dobeneck H. Liebigs Ann. 1971; 751: 50
• 5a Emmett JC, Lwowski W. Tetrahedron 1966; 22: 1011
• 5b Theilacker W, Blum HJ, Heitmann W, Kalenda H, Meyer HJ. Justus Liebigs Ann. Chem. 1964; 673: 96
• 6a Fletcher H. Tetrahedron 1966; 22: 2481
• 6b Bender CO, Bonett R. J. Chem. Soc., Chem. Commun. 1966; 198
• 7a Lash TD, Novak BH, Lin Y. Tetrahedron Lett. 1994; 35: 2493
• 7b Murashima T, Fujita K, Ono K, Ogawa T, Uno H, Ono N. J. Chem. Soc., Perkin Trans.1 1996; 1403
• 8a Bastrakov MA, Starosotnikov AM, Pechenkin SYu, Kachala VV, Glukhov IV, Shevelev SA. J. Heterocycl. Chem. 2010; 47: 893
• 8b Starosotnikov AM, Bastrakov MA, Pechenkin SY, Leontieva MA, Kachala VV, Shevelev SA. J. Heterocycl. Chem. 2011; 48: 824
• 8c Konstantinova LS, Bastrakov MA, Starosotnikov AM, Glukhov IV, Lysov KA, Rakitin OA, Shevelev SA. Mendeleev Commun. 2010; 20: 353
• 8d For a recent review, see: Terrier F, Dust JM, Buncel E. Tetrahedron 2012; 68: 1829
• 9 Lee S, Chataigner I, Piettre SR. Angew. Chem. Int. Ed. 2011; 59: 472
• 10 Pechenkin SY, Starosotnikov AM, Bastrakov MA, Glukhov IV, Shevelev SA. Russ. Chem. Bull. Int. Ed. 2012; in press; Izv. Akad. Nauk. Ser. Khim. 2012, 1, 73
• 11 Pechenkin SY, Starosotnikov AM, Bastrakov MA, Kachala VV, Shevelev SA. Mendeleev Commun. 2012; 22: 35
• 12 Crystallographic data of 3b and 13b crystals have been deposited at the Cambridge Crystallographic Data Centre (CCDC) with the reference numbers 874401 and 874402, respectively. These data can be obtained free of charge via http://www.ccdc.cam.uk/conts/retrieving.html
• 13a Buncel E, Crampron MR, Strauss MJ, Terrier F. Electron-Deficient Aromatic- and Heteroaromatic-Base Interactions. Elsevier; Amsterdam: 1984
• 13b Sugimoto N, Sasaki M, Osugi J. J. Chem. Soc., Perkin Trans. 1 1984; 655
• 13c Shipp KC, Kaplan LA, Sitzmann ME. J. Org. Chem. 1972; 37: 1966
• 14 Rozhkov VV, Kuvshinov AM, Gulevskaya VI, Chervin II, Shevelev SA. Synthesis 1999; 2065
• 15 Hoyer H, Vogel M. Monatsh. Chem. 1962; 93: 766