121632-87-9

Upstream product

• 106-49-0 p-toluidine 
• 247179-01-7 2-tert-butoxycarbonylamino-3-phenyl-propionic acid isobutyl ester 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 

Downstream Products

• 21171-98-2 (2S)-2-amino-N-(4-methylphenyl)-3-phenylpropanamide 
• 479191-79-2 (2R,5S)-1-(1H-1,2,3-benzotriazol-1-ylmethyl)-5-benzyl-3-(4-methylphenyl)-2-phenyltetrahydro-4H-imidazol-4-one 
• 479191-75-8 (2R,5S)-5-benzyl-3-(4-methylphenyl)-2-phenyltetrahydro-4H-imidazol-4-one 
• 479191-76-9 (2S,5S)-5-benzyl-3-(4-methylphenyl)-2-phenyltetrahydro-4H-imidazol-4-one 
• 433219-34-2 (2S)-N¹-(4-methylphenyl)-3-phenyl-1,2-propanediamine 
• 479191-68-9 (2S)-2-[(1H-1,2,3-benzotriazol-1-ylmethyl)amino]-N-(4-methylphenyl)-3-phenylpropanamide 

Relevant academic research and scientific papers

Facile N-Derivatization of α-Amino Esters and Amides via Benzotriazolylmethyl Derivatives

α-(N-Substituted amino)esters were prepared in a two-step procedure from available unsubstituted α-amino esters. α-Amino esters are first converted into the corresponding N-benzotriazolylmethyl derivatives; in the second step, the benzotriazole group is substituted by various nucleophiles with or without the presence of a Lewis acid to give substituted α-amino esters in high overall yield under mild conditions with no signs of racemization. Boc-protected amino acids were converted into α-amino amides; subsequent deprotection allowed the conversion into N-substituted derivatives analogously to the α-amino esters, without racemization in high yields under mild conditions.

Syntheses of optically active tetrahydro-1H-pyrrolo[1,2-a]imidazol-2-ones and hexahydroimidazo[1,2-a]pyridin-2(3H)-ones

The reactions of (2S)-2-amino-2-substituted-N-(4-nitrophenyl)acetamides 16a-c, succindialdehyde (13), and benzotriazole afforded enantiopure (3S,5R,7aR)-5-(1H-1,2,3-benzotriazol-1-yl)-3-substituted-1-(4-nitrophenyl) tetrahydro-1H-pyrrolo[1,2-a]imidazol-2-ones 17a-c, which were converted by sodium borohydride into (3S,7aR)-3-substituted-1-(4-nitrophenyl)tetrahydro-1H-pyrrolo[1, 2-a]imidazol-2-ones 18a-c. Chiral (2S)-2-amino-2-substituted-N-(4-methylphenyl)acetamides 12a-d, easily prepared in two steps from N-Boc-α-amino acids 10a-d, similarly reacted with glutaraldehyde (20) and benzotriazole to generate 5-benzotriazolyl-3-substituted-hexahydroimidazo[1,2-a]pyridin 2(3H)-ones 21a-d, which were converted by sodium borohydride directly into optically active 3-substituted-hexahydroimidazo[1,2-a]pyridin-2(3H)-ones 22a-d.

Stereoselective syntheses of chiral (3S,9bS)-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones

Chiral (3S,9bS)-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones 11a-11f, 14b,14c and 17a,b were prepared in 78-93% yields with high stereoselectivities (d.e. >99%) by the intermolecular condensations of 2-formylbenzoic acids 10 or 13 or 2-acetylbenzoic acid 15 with chiral diamines 9a-9f and 9h. Compounds 9a-9f and 9h were readily prepared in three steps from optically active N-Boc-α-amino acids 5a-5d.

Convenient syntheses of unsymmetrical imidazolidines

Unsymmetrical imidazolidines 10-14, optically active imidazolidines 20-22, and 2,3-dihydro-1H benzimidazoles 28 and 29 were synthesized in good to excellent yields by Mannich reactions of 1,2-ethanediamines 8a-c, 18a-c, or N-methyl-1,2-benzenediamine (26a) with benzotriazole and formaldehyde, followed by the nucleophilic substitution of the benzotriazolyl group with C- nucleophiles (Grignard reagents, sodium cyanide), an S-nucleophile (benzenethiol), and a P-nucleophile (triethyl phosphite).

Novel syntheses of enantiopure hexahydroimidazo[1,5-b]isoquinolines and tetrahydroimidazo[1,5-b]isoquinolin-1(5H)-ones via iminium cation cyclizations

Condensations of chiral diamines 11a-c with benzotriazole and formaldehyde gave benzotriazolyl intermediates 12a-c; similar condensations of α-amino-amides 10a-c with benzotriazole and paraformaldehyde gave 14a-c. Subsequent treatment of 12a-c and 14a-c with AlCl3 led to enantiopure tricyclic 1,2,3,5,10,10a-hexahydroimidazo[1,5-b]isoquinolines 1a-c and 2,3,10,10a-tetrahydroimidazo[1,5-b]isoquinolin-1(5H)-ones 15a-c, respectively, via Lewis acid promoted iminium cation cyclizations.

Stereoselective syntheses of 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-diones

1H-Imidazo[2,1-a]isoindole-2,5(3H,9bH)-diones 6a-i are synthesized in 67-96% yields with high stereoselectivities (de 88-99%, except 6e with a 58% de value) via intermolecular condensation of 2-formylbenzoic acid (5) and α-amino amides 4a-i in the presence of a catalytic amount of toluene-p-sulfonic acid. Intermediates 4 are obtained in two steps from easily available chiral N-Boc-α-amino acids 1.