REFERENCES
- Bentley , K. W. β-Phenylethylamines and the isoquinoline alkaloids . Nat. Prod. Rep. 2006 , 23 ( 3 ), 444 – 463 .
- For recent examples, see (a) Alper , P. ; Azimioara , M. ; Cow , C. ; Epple , R. ; Jiang , S. ; Lelais , G. ; Michellys , P.-Y. ; Nguyen , T. N. ; Westscott-Baker , L. ; Wu , B. Tetrahydroisoquinoline compounds and compositions as modulators of GPR119 activity and their preparation . WO Patent 2008097428, 2008; (b) Cowan , D. J. ; Larkin , A. L. ; Zhang , C. ; Musso , D. L. ; Green , G. M. ; Cadilla , R. ; Spearing , P. K. ; Bishop , M. J. ; Speake , J. D. Preparation of di(hetero)aryls as antagonists or inverse agonists at opioid receptors . WO Patent 2008021849, 2008; (c) Habashita , H. ; Nakade , S. ; Preparation of heterocyclic compounds having sphingosine-1-phosphate (S1P) receptor binding potency . WO Patent 2006001463, 2006; (d) Ueno , H. ; Yokota , K. ; Hoshi , J.-I. ; Yasue , K. ; Hayashi , M. ; Hase , Y. ; Uchida , I. ; Aisaka , K. ; Katoh , S. ; Cho , H. Synthesis and structure–activity relationships of novel selective factor Xa inhibitors with a retrahydroisoquinoline ring . J. Med. Chem. 2005 , 48 ( 10 ), 3586 – 3604 ; (e) Babin , D. ; Benedetti , Y. ; Chatreaux , F. ; Weston , J. B. Preparation of novel 1,2,3,4-tetrahydrosioquinolines for use as fungicides . WO Patent 2001074808 , 2001 .
- (a) Selnick , H. G. ; Smith , G. R. ; Tebben , A. J. An improved procedure for the cyanation of aryl triflates: A convenient synthesis of 6-cyano-1,2,3,4-tetrahydroisoquinoline . Synth. Commun. 1995 , 25 ( 20 ), 3255 – 3261 ; (b) Baldwin , J. J. ; Claremon , D. A. ; Ponticello , G. S. ; Selnick , H. G. Spirobenzopyrancyclohexanes as class III antiarrhythmic agents . US Patent 5403846 , 1995 .
- Buck , J. S. Some substituted tetrahydroisoquinoline hydrochlorides . J. Am. Chem. Soc. 1934 , 56 , 1769 – 1771 .
- Bates , H. A. ; Bagheri , K. ; Vertino , P. M. Effect of pH on the regioselectivity of Pictet–Spengler reactions of 3-hydroxyphenethylamine with formaldehyde and acetaldehyde . J. Org. Chem. 1986 , 51 , 3061 – 3063 .
- Ornstein , P. L. ; Arnold , M. B. ; Augenstein , N. K. ; Paschal , J. W. Syntheses of 6-oxodecahydroisoquinoline-3-carboxylates: Useful intermediates for the preparation of conformationally defined excitatory amino acid antagonists . J. Org. Chem. 1991 , 56 , 4388 – 4392 .
- Verschueren , K. ; Toth , G. ; Tourwe , D. ; Lebl , M. ; Van Binst , G. ; Hruby , V. A facile synthesis of 1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid, a conformationally constrained tyrosine analogue . Synthesis 1992 , 458 .
- Liu , C. ; Thomas , J. ; Brieaddy , L. ; Berrang , B. ; Carroll , I. An improved synthesis of (3R)-2-(tert-butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid . Synthesis 2008 , 6 , 856 .
- Consult MSDS for formaldehyde and Bretherick's Handbook of Reactive Chemical Hazards, , 6th ed. ; P. G. Urben (Ed.); Butterworth-Heinemann : Oxford , 1999 .
- Fieser , L. F. ; Fieser , M. Reagents for Organic Synthesis ; Wiley : New York , 1967 ; vol. 1 , p. 450 .
- Echavarren , A. M. ; Stille , J. K. Palladium-catalyzed coupling of aryl triflates with organostannanes . J. Am. Chem. Soc. 1987 , 109 , 5478 .
- Frantz , D. E. ; Weaver , D. G. ; Carey , J. P. ; Kress , M. H. ; Dolling , U. H. Practical synthesis of aryl triflates under aqueous conditions . Org. Lett. 2002 , 4 ( 26 ), 4717 .
- Hendrickson , J. B. ; Bergeron , R. Triflamides: New acylating and triflating reagents . Tetrahedron Lett. 1973 , 46 , 4607 .