Acylcyanamides: Versatile Synthetic Intermediates

References

• Taylor , W. L. and Battersby , A. R. , eds. 1967 . Oxidative Coupling of Phenols , New York : Marcel Dekker, Inc. .
   Google Scholar
• Cadiot , P. and Chodkiewicz , W. 1969 . Acetylenes , Edited by: Viehe , H. G. 597 – 647 . New York : Marcel Dekker, Inc. .
   Google Scholar
• Eglinton , G. and McCrae , W. 1963 . Adv. Org. Chem. , 4 : 225
   Google Scholar
• Hampton , K. G. and Christie , J. J. 1975 . J. Org. Chem. , 40 : 3887
   Web of Science ®Google Scholar
• Paquette , L. A. , Snow , R. A. , Muthard , J. L. and Cynkowski , T. 1978 . J. Am. Chem. Soc. , 100 : 1600
   Google Scholar
• Frazier , R. H. Jr. and Harlow , R. L. 1980 . J. Org. Chem. , 45 : 5408
   Web of Science ®Google Scholar
• Kobayashi , Y. , Taguchi , T. and Morikawa , T. 1978 . Tetrahedron Lett. , : 3555
   Google Scholar
• Ito , Y. , Konoike , T. and Saegusa , T. 1975 . J. Am. Chem. Soc. , 97 : 649
   Web of Science ®Google Scholar
• Ito , Y. , Konoike , T. , Harada , T. and Saegusa , T. 1977 . J. Am. Chem. Soc. , 99 : 1487
   Web of Science ®Google Scholar
• Kaiser , E. M. 1967 . J. Am. Chem. Soc. , 89 : 3659
   Google Scholar
• Kauffmann , T. 1974 . Angew. Chem. Int. Ed. Engl. , 13 : 291
   Google Scholar
• Maryanoff , C. A. , Maryanoff , B. E. , Tang , R. and Mislow , K. 1973 . J. Am. Chem. Soc. , 95 : 5839
   Google Scholar
• Vijh , A. K. and Conway , B. E. 1967 . Chem. Rev. , 67 : 623
   Web of Science ®Google Scholar
• Weedon , B. C. L. 1952 . Q. Rev. Chem. Soc. , 6 : 380
   Web of Science ®Google Scholar
• Weedon , B. C. L. 1960 . Adv. Org. Chem. , 1 : 1
   Google Scholar
• Kofron , W. G. and Hauser , C. R. 1970 . J. Org. Chem. , 35 : 2085
   Web of Science ®Google Scholar
• Rathke , M. W. and Lindert , A. 1971 . J. Am. Chem. Soc. , 93 : 4605
   Web of Science ®Google Scholar
• Brocksom , T. J. , Petragnani , N. , Rodrigues , R. and LaScala , H. Teixeira . 1975 . Synthesis , : 396
   Google Scholar
• Kobayashi , Y. , Taguchi , T. , Morikawa , T. , Tokuno , E. and Sekiguchi , S. 1980 . Chem. Pharm. Bull. , 28 : 262
   Google Scholar
• Chung , S. K. and Dunn , L. B. Jr. 1983 . J. Org. Chem. , 48 : 1125
   Web of Science ®Google Scholar
• Belletire , J. L. , Spletzer , E. G. and Pinhas , A. R. 1984 . Tetrahedron Lett. , 25 : 5969
   Web of Science ®Google Scholar
• Belletire , J. L. and Fremont , S. L. 1986 . Tetrahedron Lett. , 27 : 127
   Web of Science ®Google Scholar
• Belletire , J. L. and Fry , D. F. 1987 . J. Org. Chem. , 52 : 2549
   Web of Science ®Google Scholar
• Belletire , J. L. and Fry , D. F. 1988 . J. Org. Chem. , submitted
   PubMed Web of Science ®Google Scholar
• Belletire , J. L. , Fremont , S. L. and Fry , D. F. 1988 . Synth. Commun. , 18 in press
   Google Scholar
• Belletire , J. L. and Spletzer , E. G. 1986 . Tetrahedron Lett. , 27 : 131
   Web of Science ®Google Scholar
• Belletire , J. L. and Fry , D. F. 1988 . Synth. Commun. , 18 : 29
   Web of Science ®Google Scholar
• Kwon , C.-H. , Nagasawa , H. T. , DeMaster , E. G. and Shirota , F. N. 1986 . J. Med. Chem. , 29 : 1922
   PubMed Web of Science ®Google Scholar
• Apparently, addition of aqueous acid to the borane solution converts the intermediate imine to the formamide which, in turn, is then rapidly reduced to the N-Me derivative by the residual borane still present. An alternative procedure in which cyclohexene is added prior to addition of the aqueous acid appears to afford moderately clean conversion to the desired corresponding primary amine 8. Nevertheless, this methodology still requires considerably more optimization (which is in progress)
   Google Scholar
• All compounds gave satisfactory spectroscopic and chromatographic analytical results
   Google Scholar