Intramolecular Hetero-Diels-Alder Reaction of Vinylallenes and Imines: Synthesis of 9-Methyl-1,2,3,4,5,6,7,8-octahydroacridine

Abstract

The intramolecular hetero-Diels-Alder reaction of vinyl­allenes and imines has been carried out. Depending on the substit­uents on the allene and the length of the tether linking diene and heterodienophile, the reaction proceeds thermally or with Lewis acid activation. The transformation of one of the adducts into a 9-substituted octahydroacridine is reported.

vinyl allenes - intramolecular reaction - hetero-Diels-Alder reaction - imines - cycloaddition

References

1

The term semicyclic refers to a dienic or vinylallenic system in which only one of the double bonds is a part of a cycle.

2 Regas D. Afonso MM. Galindo A. Palenzuela JA. Tetrahedron Lett.  2000,  41:  6781 

3 Regas D. Afonso MM. Rodríguez ML. Palenzuela JA. J. Org. Chem.  2003,  68:  7845 

4 Roush WR. Intramolecular Diels-Alder Reactions, In Comprehensive Organic Synthesis   Vol. 5:  Trost BM. Fleming I. Paquette LA. Pergamon; Oxford: 1991.  p.513-550  

5a Trost BM. Lautens M. Hung M. Carmichael C. J. Am. Chem. Soc.  1984,  106:  7641 

5b Rigby J. Tetrahedron Lett.  1982,  23:  1863 

5c Rigby J. Wilson J. J. Am. Chem. Soc.  1984,  106:  8217 

5d Rigby J. Wilson J. Senanayake C. Tetrahedron Lett.  1986,  27:  3329 

5e Snider BB. Liu T. J. Org. Chem.  2000,  65:  8490 

6 Regas D. Ruiz JM. Afonso MM. Galindo A. Palenzuela JA. Tetrahedron Lett.  2003,  44:  8471 

7 Okamura WH. Curtin ML. Synlett  1990,  1 

8

All compounds described in this paper were prepared in racemic form.

9a Green T. Wuts PGM. Protective Groups in Organic Chemistry   Wiley; New York: 1991.  p.364-366  

9b Midland MM. Afonso MM. J. Am. Chem. Soc.  1989,  111:  4368 

10a Pilato ML. Catalano VJ. Bell TW. J. Org. Chem.  2001,  66:  1525 

10b Kamata K. Tominaga Y. Tori-i A. Thiemann T. Matake S. Hetereocycles  1998,  48:  1663