5-Bromo-3-[5-(3,4-dichlorophenyl)-2,3-dihydro-1H-pyrrolizin-6-yl]-1,3-dihydro-2H indol-2-one

 



5-Bromo-3-[5-(3,4-dichlorophenyl)-2,3-dihydro-1H-pyrrolizin-6-yl]-1,3-dihydro-2H
indol-2-one (7a): orange powder, 22%, mp 215-216 C. MS (m/z) (%): 462 (M+, 52), 435 (45),
405 (8), 353 (12), 317 (18), 289 (52), 208 (30), 173 (33), 127 (46), 75 (30), 41 (100). Anal.
calcd. for C21H15BrСl2N2O (462.17): C 54.57; H 3.27; N 6.06; Found: C 54.48; H 3.19; N 6.10.


1595284-00-6

C21 H15 Br Cl2 N2 O

2H-​Indol-​2-​one, 5-​bromo-​3-​[5-​(3,​4-​dichlorophenyl)​-​2,​3-​dihydro-​1H-​pyrrolizin-​6-​yl]​-​1,​3-​dihydro-

Molecular Weight

462.17

NOESY








 

 





Beilstein Journal of Organic Chemistry (2014), 10, 117-126
http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-10-8

Scheme 2: The synthesis of compounds 7a–7c.

Figure 7: The selected COSY, NOESY and HMBC correlations of the signals in the 1H and 13C NMR spectra of compound 7a.

The tentative mechanism for the formation of 7a is outlined in Scheme 3. First, the initially formed spiropyrrolizidine undergoes decarboxylation via ring opening of the spiro cycle. The subsequent enolization of the intermediate leads to the formation of the dihydropyrrolizinyl oxindole system.

Scheme 3: Tentative reaction mechanism for the decarboxylative cyclative rearrangement of the initial three-component product.

 7a: orange powder, 22%, mp 215–216 °C. 1H (500 MHz, DMSO-d6) and 13C NMR (125 MHz, DMSO-d6) data are given in Table 3. MS (m/z) (%): 462 (M+, 52), 435 (45), 405 (8), 353 (12), 317 (18), 289 (52), 208 (30), 173 (33), 127 (46), 75 (30), 41 (100); anal. calcd for C21H15BrСl2N2O (462.17): C 54.57; H 3.27; N 6.06; found: C 54.48; H 3.19; N 6.10.


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Clc1ccc(cc1Cl)c2c(cc3CCCn23)C4c5cc(Br)ccc5NC4=O




 Angkor Thom, Angkor, Cambodia
 ANGKOR RUINS, CAMBODIA

 
 
























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 At Angkor Wat- Templo De Angkor- Siem Reap- Camboya.

 

Map of the Khmer Empire (in red) in 900 AD 

 
 

 

 
 
 
 
 
 





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