Type: Article

Unique cascade ring-opening/cyclization reaction of azlactones and DBU or DBN: Synthesis of new pyrrolam A analogues

Journal: Tetrahedron (14645416)Year: 2017Volume: 73Issue: Pages: 1397 - 1406

Parhizkar G. Khosropour A.R.Mohammadpoor Baltork I.^a Parhizkar E.Amiri Rudbari H.^a

a :University of Isfahan - IRAN(IR) - Isfahan

DOI:10.1016/j.tet.2017.01.036Language: English

Abstract

1-Azabicyclo[3.3.0]oct-3-en-2-one derivatives were synthesized efficiently through the facile cascade reaction of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) with arylidene azlactones. This research provides a straightforward procedure for the synthesis of a novel class of multicyclic semi-alkaloids which shows good antimicrobial activity. Under catalyst-free, mild, and solventless condition, a wide range of fused tricyclic derivatives was obtained in high yields. © 2017 Elsevier Ltd

Author Keywords

AzlactoneDBNDBUPyrrolam A analogueSolvent-free

Other Keywords

1,4 bis [n (3 oxo dodecahydropyrrolo[2' ,1':2,3]pyrimido[1,2 a]azepin 2 yl)benzamide]benzene1,5 diazabicyclo[4.3.0]non 5 ene1,8 diazabicyclo[5.4.0]undec 7 ene2 chloro n [1 (4 chlorophenyl) 3 oxo dodecahydropyrrolo[2' ,1':2,3]pyrimido[1,2 a]azepin 2 yl]benzamide2 chloro n [1 (4 methoxyphenyl) 3 oxo dodecahydropyrrolo[2' ,1':2,3]pyrimido[1,2 a]azepin 2 yl]benzamide4 arylidene 2 aryl 5(4h)oxazoloneamidineamino acidantiinfective agentn [1 (1,4 dichlorophenyl) 3 oxo dodecahydropyrrolo[2' ,1':2,3]pyrimido[1,2 a]azepin 2 yl]benzamiden [1 (2,6 dichlorophenyl) 3 oxo dodecahydropyrrolo[2' ,1':2,3]pyrimido[1,2 a]azepin 2 yl]benzamiden [1 (3 bromophenyl) 3 oxo dodecahydropyrrolo[2' ,1':2,3]pyrimido[1,2 a]azepin 2 yl] 4 nitrobenzamiden [1 (3 bromophenyl) 3 oxo dodecahydropyrrolo[2' ,1':2,3]pyrimido[1,2 a]azepin 2 yl]benzamiden [1 (3,4 difluorophenyl) 3 oxo dodecahydropyrrolo[2' ,1':2,3]pyrimido[1,2 a]azepin 2 yl]benzamiden [1 (4 chlorophenyl) 3 oxo dodecahydropyrrolo[2' ,1':2,3]pyrimido[1,2 a]azepin 2 yl] 4 methylbenzamiden [1 (4 chlorophenyl) 3 oxo dodecahydropyrrolo[2' ,1':2,3]pyrimido[1,2 a]azepin 2 yl]benzamiden [1 (4 cyanophenyl) 3 oxo dodecahydropyrrolo[2' ,1':2,3]pyrimido[1,2 a]azepin 2 yl]benzamiden [1 (4 fluorophenyl) 3 oxo dodecahydropyrrolo[2' ,1':2,3]pyrimido[1,2 a]azepin 2 yl]benzamiden [1 (4 methoxyphenyl) 3 oxo dodecahydropyrrolo[2' ,1':2,3]pyrimido[1,2 a]azepin 2 yl]benzamiden [1 (4 nitrophenyl) 3 oxo dodecahydropyrrolo[2' ,1':2,3]pyrimido[1,2 a]azepin 2 yl] 4 nitrobenzamiden [1 (4 nitrophenyl) 3 oxo dodecahydropyrrolo[2' ,1':2,3]pyrimido[1,2 a]azepin 2 yl]benzamiden [1 (naphthalen 2 yl) 3 oxo dodecahydropyrrolo[2' ,1':2,3]pyrimido[1,2 a]azepin 2 yl]benzamiden [3 oxo 1 (thiophen 2 yl)dodecahydropyrrolo[2' ,1':2,3]pyrimido[1,2 a]azepin 2 yl]benzamidepenicillin derivativepyrrolam A analoguepyrrolizidine alkaloidstreptomycintetracyclineunclassified drugantimicrobial activityArticleAspergillus flavusCandida albicanscarbon nuclear magnetic resonancecatalystcyclizationdrug synthesiselectronEscherichia coligrowth inhibitioninhibition zonenucleophilicityprecursorpriority journalproton nuclear magnetic resonancereaction analysisring openingsolvent effectStaphylococcus aureustautomerizationX ray diffraction