5036-62-4

Upstream product

• 107-10-8 propylamine 
• 292638-85-8 acrylic acid methyl ester 

Downstream Products

• 18009-71-7 3-[(5-Bromo-3-chloro-2-diacetylamino-benzyl)-propyl-amino]-propionic acid methyl ester 
• 307964-83-6 methyl 3-(benzoylpropylamino)propanoate 
• 1431558-11-0 C₁₇H₂₅N₃O₃ 
• 1431558-04-1 C₂₂H₃₃N₃O₅ 
• 1431557-96-8 C₂₁H₃₁N₃O₅ 
• 1431557-92-4 C₁₆H₂₃N₃O₃ 
• 1431557-89-9 C₁₈H₂₇NO₇S 
• 1431557-86-6 C₁₇H₂₅NO₅ 
• 1431557-83-3 C₁₇H₂₃NO₅ 
• 1431557-80-0 C₁₄H₁₉NO₄ 
• 1357061-83-6 3-(4-chlorophenyl)-1-propyl-2-thioxotetrahydropyrimidin-4(1H)-one 
• 307964-82-5 4-(benzoylpropylamino)-1-diazobutan-2-one 

Relevant academic research and scientific papers

Aza-Michael reaction: Selective mono- versus bis-addition under environmentally-friendly conditions

Aza-Michael reactions between primary amines and methyl propenoate have been investigated under environmentally-friendly solventless heterogeneous catalysis in order to obtain the mono- or the bis-adduct. The reaction conditions can be altered so as to maximise the yields of the required product with high selectivity.

Synthesis of tetrahydropyrazolo[1,5- C ]pyrimidine-2,7(1 H,3 H)-diones

A series of tetrahydropyrazolo[1,5-c]pyrimidine-2,7(1H,3H)-diones 3a-h as the first representatives of the so far unexplored saturated heterocyclic system have been synthesized, formally in 12 steps from methyl acrylate (4). The synthesis comprises a four-step preparation of methyl N-Cbz-5-alkylamino-3- oxopentanoates 9a-c, their three-step transformation into 5-{2-[(alkyl) (benzyloxycarbonyl)amino]ethyl}pyrazolidin-3-ones 12a-c, three-step selective alkylation of the amidic N-2 to give 2-alkyl-5-{2-[(alkyl)(benzyloxycarbonyl) amino]ethyl}pyrazolidin-3-ones 16b-h, followed by hydrogenolytic Cbz-deprotection and subsequent cyclization of the intermediate 1,4-diamine with CDI to furnish the title compounds 3. Most of the synthetic steps were performed as a one-pot transformation. Georg Thieme Verlag Stuttgart New York.

Sterically controlled stereoregulation in aldol reactions of 3-aryl-1-alkyl dihydrothiouracils

Aldol reactions of 3-aryl-1-alkyl dihydrothiouracils were investigated with respect to the orientation of the exocyclic group at N1, electronic effects of the aryl substituent at N3 and the steric demands of the electrophile. The reactions highlight the preference for formation of the anti aldol diastereomer with increasing steric constraints of the reactants. Georg Thieme Verlag Stuttgart · New York.

Rhodium(II)-catalyzed cyclization of amido diazo carbonyl compounds

A series of acyclic diazo ketoamides were prepared from N-benzoyl-N-alkylaminopropanoic acids and were treated with a catalytic amount of rhodium(II) acetate. The resultant carbenoids underwent facile cyclization onto the neighboring amide carbonyl oxygen atom to generate seven-membered carbonyl ylide dipoles. Subsequent collapse of the dipoles with charge dissipation produce bicyclic epoxides which undergo further reorganization to give substituted 5-hydroxydihydropyridones in good yield. Depending on the nature of the substituent groups, it was possible to trap some of the initially formed carbonyl ylide dipoles with a reactive dipolarophile such as DMAD. In other cases, cyclization of the dipole to the epoxide is much faster than bimolecular trapping. A related cyclization/rearrangement sequence occurred when diazo ketoamides derived from the cyclic pyrrolidone and piperidone ring systems were subjected to catalytic quantities of Rh(II) acetate. With these systems, exclusive O-cyclization of the amido group onto the carbenoid center occurs to generate a seven-ring carbonyl ylide dipole. Starting materials are easily prepared, and the cascade sequence proceeds in good yield and does not require special precautions. The overall procedure represents an efficient one-pot approach toward the synthesis of various indolizidine and quinolizidine ring systems.