A new and practical boronic acid catalyzed intramolecular cyclodehydration of ureas for the synthesis of LFA-1 antagonists

Tetrahedron Letters

Volumn 52, Issue 19, 2011, Pages 2465-2467

  Frutos, Rogelio P ^a   Tampone, Thomas ^a   Mulder, Jason A ^a   Xu, Yibo ^a   Reeves, Diana ^a   Wang, Xiao Jun ^a   Zhang, Li ^a   Krishnamurthy, Dhileepkumar ^a   Senanayake, Chris H ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1H IMIDAZO[1,2 A]IMIDAZOL 2 ONE 1 ANTAGONIST; AMIDE; BORONIC ACID DERIVATIVE; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG; UREA;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; DECOMPOSITION; DRUG SYNTHESIS;

EID: 79953715127     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.03.007     Document Type: Article

References (13)

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11. 3) δ 1.27 (s, 3H); 3.00-3.60 (m, 4H), 3.34 (s, 6H), 4.39 (dd, J = 5.6, 5.6 Hz, 1H), 6.12 (dd, J = 6.0, 6.0 Hz, 1H), 6.23 (s, 1H), 7.28 (dd, J = 2.0, 2.0 Hz, 1H), 7.33-7.37 (m, 2H), 7.77-7.81 (m, 2H), 7.81 (d, J = 2.0, 2.0 Hz, 2H) 9.98 (s, 1H).
12. 3 solution. The organic layer was collected and concentrated under reduced pressure (rotorvap) to afford the desired crude product as an amber oil in 80-95% assay yield.
13. 3) δ 1.80 (s, 3H), 3.26 (d, J = 13.6 Hz, 1H), 3.39 (d, J = 13.6 Hz), 6.94 (d, J = 1.2 Hz, 1H), 6.97 (d, J = 1.2 Hz, 1H), 7.01 (d, J = 8.4 Hz, 2H), 7.26 (t, J = 1.8 Hz, 1H), 7.46 (d, J = 8.4 Hz, 2H), 7.75 (d, J = 1.8 Hz, 2H).