84671-75-0Relevant academic research and scientific papers
Structure reassignment and synthesis of jenamidines A1/A 2, synthesis of (+)-NP25302, and formal synthesis of SB-311009 analogues
Duvall, Jeremy R.,Wu, Fanghui,Snider, Barry B.
, p. 8579 - 8590 (2007/10/03)
The proposed structures of jenamidines A, B, and C (1-3) were revised to jenamidines A1/A2, B1/B2, and C (8-10). Jenamidines A1/A2 (8) were synthesized from activated proline derivative 43 by conversion to 26 in two steps and 50% overall yield. Acylation of 26 with acid chloride 38d gave 39d, which was deprotected with TFA and then mild base to give 8 in 45% yield from 26. (-)-trans-2,5- Dimethylproline ethyl ester (49) was prepared by the enantioselective Michael reaction of ethyl 2-nitropropionate (51) and methyl vinyl ketone (50) using modified dihydroquinine 60 as the catalyst. Further elaboration converted 49 to natural (+)-NP25302 (12). A Wittig reaction of proline NCA (76) with ylide 79 gave 72 as a 9/1 E/Z mixture in 27% yield, completing a one-step formal synthesis of SB-311009 analogues.
EXTRUSION REACTIONS-VI. TRANSFORMATIONS OF BETA(4-QUINAZOLINYLTHIO)KETONES TO 3-(BETA KETOALKYL)-4(3H)-QUINAZOLONE DERIVATIVES
Singh, Harjit,Deep, Kanwal
, p. 4937 - 4940 (2007/10/02)
4-(4-Quinazolinylthio)-butan-2-one and 3-(4-quinazolinylthio) propiophenone (4, R=CH3, C6H5) with POCl3 give 3-(3-oxobutyl)-4(3H)-quinazolone and 3-(2-benzoylethyl)-4(3H)-quinazolone (7, R=CH3, C6H5, X=O) via S N rearrangement followed by =C=S to =C=O conversion.Non-protic heterocyclic thioamides undergo similar oxidation.
A Novel Phosphorus Oxychloride Induced Conversion of β-(4-Quinazolinylthio) Ketones into β- Ketones
Bal, Mohinder S.,Deep, Kanwal,Singh, Harjit
, p. 805 - 806 (2007/10/02)
β-(4-Quinazolinylthio)ketones have been converted into β- ketones on refluxing their solutions in phosphorus oxychloride.
