By Heinz A. Staab, H. Bauer, K. M. Schneider
Within the overdue fifties and early sixties H. A. Staab came across N,N'-carbonyl-diimidazole (CDI), its analogues, and the family members of azolides derived from them. quickly those compounds turned largely preferred as man made development blocks of unsurpassed variety. The spectrum of gear, that may be received 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, with his coauthors H. Bauer and ok. M. Schneider, has amassed their practise, houses, and manifold purposes in a entire and topical overview.
Are you within the box of synthesis of ordinary items, biomolecules, heterocycles, or different complex natural compounds? Then, your first look could good be into 'Staab'- this guide must always be nearby of your table or lab bench.
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Additional resources for Azolides in Organic Synthesis and Biochemistry
142] Method A: R'CO,H 1.  Under the following conditions, which are free of any acids and stronger bases no racemization was observed. , _ .. C02H ©^ 9 N-C-N N-CH3 > CH3-N N-C-R 1 \=/ \=/ CH 3 N0 2 ,5min. \=/ R2OH 3h > R'CO^2 CF3S03G 2CF3SO3e RJC02H R2OH C6H5C02H Z-Phe Z-Phe Z-Phe Z-Gly Z-Ala C6H5CH2OH C2H5OH C18H37OH 1-menthol ± CH3CH(OH)C02C2H5 Yield of R'COjR2 (%) quant.
P. (°Q 53- 55 136 -137 39- 40 81- 82 63- 64 Imidazolides H-COIm CF3-COIm CCl3-COIm C,5H3l-COIm CH3OOC- (CH2)4-COIm C6H5 / * CQIm C6H5 Yield (%) Reagent 85 CDI 70 CDI 73 CDI ImCSIm 83 CDI 75 Ref.      118 - 119 89 CDI  163 - 164 73-74 109-110 109- 110 109-110 187 - 190 95 97-100 167 148 - 150 146 - 147 97 80 95 83 84 80 70 88 84 99 75 CDI CDI CDI ImSOIm ImCSIm CDI CDI CDI CDI ImSOIm ImCSIm            112-113 80 CDI  201 - 203 92 CDI  C6H5 COIm 4-CH3C6H4-COIm 4-[(CH3)3C]C6H4-COIm 4-[(CH3)3C]C6H4-COIm 4-[(CH3)3C]C6H4-COIm 2,4,6-[(CH3)3C]3C6H2-COIm C5H4N-COIm (Isonicotinic acid) 4-(CH3)2NC6H4N* NC6H4-COIm ImCO-(CH2)2-COIm ImC(>-(CH2)4-COIm ImCO-(CH2)4-COIm H3C CH3 CH3 CH3 (Vitamin A acid imidazolide) CH3 CH3 ^COIrn ImCO CHL (Crocetin-diimidazolide) CH, 22 2 Preparation and Properties ofAzolides Table 2—1 lists some examples of carboxylic acid imidazolides of various structures prepared by the use of NjAf'-carbonyldiimidazole (GDI), A^'-thiocarbonyldiimidazole (ImnCS-Im), and A^V'-sulfinyldiimidazole (Im-SO-Im).
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).
Azolides in Organic Synthesis and Biochemistry by Heinz A. Staab, H. Bauer, K. M. Schneider