References and Notes
- Street , L. J. , Baker , R. , Davey , W. B. , Guiblin , A. R. , Jelley , R. A. , Reeve , A. J. , Routledge , H. , Sternfeld , F. , Watt , A. P. , Beer , M. S. , Middlemiss , D. N. , Noble , A. J. , Stanton , J. A. , Scholey , K. , Hargreaves , R. J. , Sohal , B. , Graham , M. I. and Matassa , V. G. 1995 . J. Med. Chem. , 38 : 1799
- Liu , L. , Cheng , H. , Chavez , C. , Matuszewski , B. K. , Guiblin , A. R. , Polvino , W. J. , Chen , T. S. and Rogers , J. D. 1994 . Identification of urinary metablites of N-N-dimethyl-2-[5-(1,2,4-triazole-1-ylmethyl)-1H-indol-3-yl] ethylamine benzoate (MK-462) in humans . presented at the American Association of Pharmaceutical Scientists Ninth Annual Meeting . November 6–11 1994 , San Diego, CA, USA. For the isolation and identification of the indole acetic acid 1, see:
- Guan , X. and Borchardt , R. T. 1994 . Tetrahedron Lett. , 35 : 3013 For a recent example of the synthesis of an indole acetic acid and references cited therein, see:
- Chen , C. , Senanayake , C. H. , Bill , T. J. , Larsen , R. D. , Verhoeven , T. R. and Reider , P. J. 1994 . J. Org. Chem. , 59 : 3738 4. For the synthesis of N,N-dimethyltryptamines using 4% H2SO4, see:
- The Fisher indole synthesis of 1 from 3-cyanopropionaldehyde dimethyl acetal and the 4-hydrazinobenzyl triazole in polyphosphoric ester followed by KOH hydrolysis gave indole acetic acid 1 in 11% overall yield.
- Chen , C. , Lieberman , D. R. , Larsen , R. D. , Reamer , R. A. , Verhoeven , T. R. , Reider , P. J. , Cottrell , I. F. and Houghton , P. G. 1994 . Tetrahedron Lett. , 35 : 6981
- Larock , R. C and Yum , E. K. 1991 . J. Am. Chem. Soc. , 113 : 6689
- Toyota , M. and Fukumoto , K. J. 1992 . Chem. Soc. Perkin Trans. I , : 547 For recent examples of the displacement of indolemetanol with cyanide species, see:
- Runti , C. and Orlando , G. 1953 . Ann. Chim. (Rome) , 43 : 308
- Coker , J. N. , Mathre , O. B. and Todd , W. H. 1963 . J. Org. Chem. , 28 : 589
- Spande , T. F. Chemistry of Heterocyclic Compounds , Edited by: Houlihan , W. J. Vol 25 , p. 1 New York : Wiley . Part III, Chap. VIII. These reactions are believed to proceed via the methylene indolenine i
- MgSO4 was used in the reaction to minimize the desilylation of 4a to 4b. This increased the recovery since 4b is lost in the aqueous phase upon partitioning of the reaction mixture between IPAc and water.
- Reaction of 4b with NaCN in EtOH-H2O gives nitrile 5 in 68% yield, which can be purified by silica gel chromatography followed by crystallization. Treatment of 8 with 2 N HCl in methanol affords to nitrile 8 in 80% yield.