DBU catalyzed cyclative amidation reaction: A convenient synthesis of C-nucleoside analogs

Synlett

Volumn , Issue 11, 2002, Pages 1779-1782

  Tewari, Neetu ^a   Mishra, Ram C ^a   Tiwari, Vinod K ^a   Tripathi, Rama P ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

C nucleosides; DBU; Dihydropyrimidinone; Tetrabutylammonium bromide

Indexed keywords

C NUCLEOSIDE; DIHYDROPYRIDINE DERIVATIVE; TETRABUTYLAMMONIUM;

AMIDATION; ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; PHYSICAL CHEMISTRY; REACTION ANALYSIS; SOLID STATE; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0036430086     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34890     Document Type: Article

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22. 2 column using a gradient of hexane-ethyl acetate (3:2) as eluent to give compound 2a (1.56 g, 95%). Similarly compounds 2b-k were synthesized in quantitative yield by reaction with the corresponding isocyanates. For the synthesis of compounds 4a,b, 2 mmoles of glycosylated β-amino esters 1 were treated with 1 mmole of diisocyanate under similar experimental conditions.
23. 2 column using a gradient of hexane-ethyl acetate (3:1) as eluent to give compound 3a. Similarly, compounds 3b-k and 5a,b were synthesized from the corresponding ureidyl derivatives 2b-k and 4a,b, respectively. The yields and reaction time are given in Table 1.
24. 2Ph, H-2, H-4), 5.95 (d, J = 3.6 Hz, 1 H, H-1), 6.98 (m, 1 H, NHAr), 7.17 (m, 7 H, ArH).
25. Physical data of C-nucleosides. Abstract