Electrochemically Induced Aza-Henry Reaction: A New, Mild, and Clean Synthesis of α-Nitroamines

Leucio Rossi; Gabriele Bianchi; Marta Feroci; Achille Inesi

doi:10.1055/s-2007-986643

LETTER

Electrochemically Induced Aza-Henry Reaction: A New, Mild, and Clean Synthesis of α-Nitroamines

Leucio Rossi*^a, Gabriele Bianchi^a, Marta Feroci^b, Achille Inesi*^b
^a Dipartimento di Chimica, Ingegneria Chimica e Materiali, Universita degli Studi, 67040 L’Aquila, Italy
Fax: +39(0862)434203; e-Mail: rossil@ing.univaq.it;
^b Dipartimento ICMMPM, Università ‘La Sapienza’, Via C. Laurenziano 7, 00161 Roma, Italy

Abstract

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Abstract

The addition reaction of nitro compounds to azomethine functions, known as the aza-Henry (or nitro-Mannich) reaction was performed electrochemically under solvent and supporting electrolyte-free conditions. Reaction yields are very good and the method is very clean, avoiding the use of any classical solvent or catalyst.

Key words

carbanions - green chemistry - imines - Michael additions - nucleophilic additions

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References

1a Wastermann B. Angew. Chem. Int. Ed. 2003, 42: 151

1b Baer HH. Urbas L. In The Chemistry of the Nitro and Nitroso Groups Part 2: Patai S. Interscience; New York: 1970. p.117

1c Erlenmeyer H. Oberlin V. Helv. Chim. Acta 1947, 30: 1329

1d Stacy GW. Morath RJ. J. Am. Chem. Soc. 1952, 74: 3885

2 O’Brien PM. Sliskovic DR. Blankley CJ. Roth BD. Wilson MW. Hamelehle KL. Krause BR. Stanfield RL. J. Med. Chem. 1994, 37: 1810

3 Lucet D. Le Gall T. Mioskowski C. Angew. Chem. Int. Ed. 1998, 37: 2580

4a Pinnick HW. Org. React. 1990, 38: 655

4b Ballini R. Petrini M. Tetrahedron 2004, 60: 1017

4c Foresti E. Palmieri G. Petrini M. Profeta R. Org. Biomol. Chem. 2003, 1: 4275

5a Pasini A. Zunini F. Angew. Chem., Int. Ed. Engl. 1987, 26: 615

5b Otsuka M. Masuda T. Haupt A. Ohno M. Shiraki T. Sugiura Y. Maeda K. J. Am. Chem. Soc. 1990, 112: 838

6a Michalson ET. Szmuszkovicz J. Prog. Drug Res. 1989, 33: 135

6b Reedijk J. Chem. Commun. 1996, 801

7a Blaser H.-U. Chem. Rev. 1992, 92: 935

7b Soai K. Niwa S. Chem. Rev. 1992, 92: 833

7c Jacobsen EN. In Catalytic Asymmetric Synthesis Ojima I. VCH; Weinheim: 1993. p.159

7d Kolb HC. Van Nieuwenhze MS. Sharpless KB. Chem. Rev. 1994, 94: 2483

8a Adams H. Anderson JC. Peace S. Pennell AMK. J. Org. Chem. 1998, 63: 9932

8b Anderson JC. Peace S. Pih S. Synlett 2000, 850

8c Yamada K.-i. Harwood SJ. Groger H. Shibasaki M. Angew. Chem. Int. Ed. 1999, 38: 3504

8d Yamada K.-i. Moll G. Shibasaki M. Synlett 2001, 980

8e Tsuritani N. Yamada K.-i. Yoshikawa N. Shibasaki M. Chem. Lett. 2002, 276

8f Qian C. Gao F. Chen R. Tetrahedron Lett. 2001, 42: 4673

8g Knudsen KR. Risgaard T. Nishiwaki N. Gothelf KV. Jørgensen KA. J. Am. Chem. Soc. 2001, 123: 5843

8h Nishiwaki N. Knudsen KR. Gothelf KV. Jørgensen KA. Angew. Chem. Int. Ed. 2001, 40: 2992

9 Anastas PT. Williamson TC. In Green Chemistry, Designing Chemistry for the Environment Anastas PT. Williamson TC. American Chemical Society; Washington / DC: 1996. p.1-17

10a Metzger JO. Angew. Chem. Int. Ed. 1998, 37: 2975

10b Toda F. Acc. Chem. Res. 1995, 28: 480

10c Tanaka K. Toda F. Chem. Rev. 2000, 100: 1025

10d Tanaka K. Solvent-Free Organic Synthesis Wiley-VCH; Weinheim: 2003.

10e Rothemberg G. Downie AP. Raston CL. Scott JL. J. Am. Chem. Soc. 2001, 123: 8701

10f Loupy A. Petit A. Hamelin J. Texier-Boullet F. Jacquault P. Mathé D. Synthesis 1998, 1213

10g Varma SR. Green Chem. 1999, 1: 43

11a Rosini G. Ballini R. Sorrenti P. Synthesis 1983, 1014

11b Kumar HMS. Subba Reddy BV. Yadav JS. Chem. Lett. 1998, 637

11c Bhattacharya A. Purohit VC. Org. Process Res. Dev. 2003, 7: 254

11d Ballini R. Bosica G. Parrini M. Chem. Lett. 1999, 1105

12 Bernardi L. Bonini BF. Capitò E. Dessole G. Comes-Franchini M. Fochi M. Ricci A. J. Org. Chem. 2004, 69: 8168

13a Bard AJ. Stratmann M. Organic Electrochemistry, In Encyclopedia of Electrochemistry Vol. 8: Schäfer HJ. Wiley-VCH; Weinheim: 2004.

13b Organic Electrochemistry Lund H. Hammerich O. Marcel Dekker; New York: 2001.

14 Palombi L. Feroci M. Orsini M. Inesi A. Chem. Commun. 2004, 1846

15a Ramage R. Atrash B. Hopton D. Parrott MJ. J. Chem. Soc., Perkin Trans. 1 1985, 1217

15b Ramage R. Hopton D. Parrott MJ. J. Chem. Soc., Perkin Trans. 1 1984, 1357

16 Jennings BW. Lovely CJ. Tetrahedron 1991, 47: 5561

17a Wang CJ. Shi M. J. Org. Chem. 2003, 68: 6229

17b Kim JN. Lee CG. Lee KY. Tetrahedron Lett. 2003, 44: 1231

17c Okino T. Nakamura S. Furukawa T. Takemoto Y. Org. Lett. 2004, 6: 625

18 Jain LS. Vishal B. Bir Sain S. J. Mol. Catal. A: Chem. 2005, 239: 92

19 Gao F. Deng M. Qian C. Tetrahedron 2005, 61: 12238