By Heinz A. Staab, H. Bauer, K. M. Schneider
Within the overdue fifties and early sixties H. A. Staab came upon N,N'-carbonyl-diimidazole (CDI), its analogues, and the kin of azolides derived from them. quickly those compounds turned generally liked as artificial construction blocks of unsurpassed range. The spectrum of drugs, that may be got through light acylation with azolides comprises esters, amides, ketones, aldehydes, in addition to heterocycles, peptides, glycosides, and nucleotides.
Now, H. A. Staab, the 'father' of those necessary compounds, along with his coauthors H. Bauer and okay. M. Schneider, has amassed their education, houses, and manifold purposes in a accomplished and topical overview.
Are you within the box of synthesis of normal items, biomolecules, heterocycles, or different advanced natural compounds? Then, your first look may good be into 'Staab'- this guide must always be nearby of your table or lab bench.
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Extra resources for Azolides in Organic Synthesis and Biochemistry
Chem. 1961, 73, 148; H. A. Staab, G. Walther, Liebigs Ann. Chem. 1962, 657, 98-103; see also W. Ried, B. M. Beck, ibid. 1961, 646, 96-100; T. J. Pullukat, G. Urry, Tetrahedron Lett. 1967, 1953-1954.  H. A. Staab, G. Walther, Liebigs Ann. Chem. 1962, 657, 104-107.  H. A. Staab, D. W. Muller, unpublished; D. W. Muller, Ph. D. Thesis, Heidelberg 1963; see also J. P. Ferris, C. H. Huang, W. J. Hagan, Nudeosides & Nucleotides 1989, 8, 407-414.  H. A. Staab, K. Wendel, B. Polenski, unpublished.
Chim. Acta 1979, 62, 1944-1951.  K. Kunieda, T. Higushi, Y. Abe, M. Hirobe, Tetrahedron Lett. 1980, 21, 3065-3066; Tetrahedron 1983, 39, 3253-3260; further references therein.  C. H. Li, Y. H. Yieh, Y. Lin, Y. Z. Lu, A. Y. Chi, C. Y. Hsing, Tetrahedron Lett. 1981, 22, 34673470.  K. Takeda, K. Tsuboyama, H. Takayanagi, R. Shirokami, M. Takeura, H. Ogura, Chem. Pharm. Bull. 1989, 37, 2334-2337; K. Takeda, K. Tsuboyama, H. Takayanaki, H. Ogura, Synthesis 1987, 560-562.  K. Baczko, D.
Bauer, K. M. Schneider Copyright© 2002 Wiley-VCHVeriag GmbH & Co. C4]> It may be conducted in two separate steps with isolation of the carboxylic acid imidazolide, but more frequently the synthesis is carried out as a one-pot reaction without isolation of the intermediate. Equimolar amounts of carboxylic acid, alcohol, and GDI are allowed to react in anhydrous tetrahydroforan, benzene, trichloromethane, dichloromethane, dimethylformamide, or nitromethane to give the ester in high yield. The solvents should be anhydrous because of the moisture sensitivity of GDI (see Chapter 2).
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