5-Ethoxycarbonyl-2-methylamino

Ethoxycarbonyl-6,7-dimethyl-2-quinoxalinecarboxylic acid 2-(l-Ethoxycarbonylethyl)-3-methoxy quinoxaline 2-(2-Ethoxycarbonylethyl)-7-methylamino-8-nitroquinoxaline... 

M3-[(ETHOXYCARBONYL)METHYLIDYNE] - and JU3- [(METHYLAMINO)CARBONYL] METHYLIDYNE -TRIS (TRICARBONYLCOBALT)... 

Aminocarbonyl-1 -ethoxycarbonyl-E16c, 562 (N-Acylier.) 2-Methoxycarbonyl-l-(methylamino-carbonyl)- E16c,579 (N-Acylier.) Carbamidsaure N-Allyl-N-nitroso- -ethylester E4, 289 (NH - N —NO)... 

Amlodipine (4-(2-chlorophenyl)-2-[2-(methylamino)ethoxymethyl]-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-f,4-dihydropyridine) is an antihypertensive, marketed... 

Dimethoxy-2-( methylamino-mslky ) pkcnyl -5-ethoxycarbonyl-3-(4-methoxy-phenyl)-l-phenyl-lH-pyrazol 55% Schmp. 200"... 

Benzoyl-2-(4-chlor-anilino)-4-phenyl- 132, 136 5-Benzoyl-2,4-dianilino- 140 2-Benzoyl-4,5-dimethyl- 261 5-Benzoyl-4-dimethylamino-2-methylamino- 140 2-(2-Benzoyl-hydrazino)-4-(ethoxycarbonyl-methyl)- 74... 

Anilino- 910 2-Benzylamino- 910 6-Ethoxycarbonyl-2-phcnyl- 922 2-Furyl- 907 2-(2-Furyl)- 911 2-Methyl- 911 2-Methylamino- 910 2-(4-Methyl-phenyl)- 911 2-Organoamino- 909 2-Phenyl- 911 2-(2-Phenyl-ethenyl)- 911 2-(2-Pyridyl)- 880 2-(2-Thienyl)- 911... 

Examples of both 2-amino-4 f-1,3-thiazines and 2-amino-6H-1,3-thiazines are known, and in the case of 2-amino-4/f-1,3-thiazines these seem to be favored over their imino tautomers, at least in solution. Thus, 4,4,6-trimethyl-2-(A-methyl-7V-phenylamino)-4H-l,3-thiazine (I), which cannot tautomerize, absorbs at = 264 nm, and 4,4,6-trimethyl-2-(iV-phenylamino)-4H-l,3-thiazine (2), which can, shows = nm. 3,4,4-Trimethyl-2-(7V-phenylimino)-4//-l,3-thiazine (3), which is locked into the imino form, shows a main UV band at = 236 nm with a shoulder at 280 nm. Many 2-amino-6/f-1,3-thiazines are known where there is an unsaturated (acyl) group at C-5. This group serves to extend the delocalization of the chromophore, and 5-ethoxycarbonyl-2-(V-methylamino)-6//-l,3-thiazine (4), for example, exhibits UV bands at A iax = 240 nm, 266 nm, and 330 nm (Figure 1) <90AHC(50)85>. 

At the University of Ottawa the work of L. Benoiton and his students, especially F.M.F. Chen, gained major importance in the study of racemization during peptide synthesis. The loss of chiral purity in activated AT-methylamino acids is one of their numerous contributions. l-Ethoxycarbonyl-2-ethoxy-l,2-dihydroquinoline (EEDQ), the coupling reagent mentioned on page 91 was introduced in 1968 by B. Belleau and Malek at Ottawa. 

R = H, D) were obtained from the 6-methyl-3-ester derivative and its 6,7,8-deuterio derivative 291 (R = Me, R = COOEt, R -R" = H, D). These derivatives were transformed into 293 (R = H, D) by heating in POCI3. Optically active 291 (R = Me, R = COOEt, R -R = H) afforded optically active 6,7-dihydro-477 294 (R = H), but optically inactive AH-pyrido[l, 2-a]pyrimidine 293 (R = Me, R = COOEt, R = H). Similarly ethyl 9-(A -phenyl-iV-methylamino)-6-methyl-4-oxo-6,7-dihydro-4/7-pyrido[l,2-a] pyrimidine-3-carboxylate gave 9-[iV-(4-formylphenyl)-A -methylamino]-7-dimethylaminomethylene-6-methyl-6,7-dihydro-4-oxo-4/f-pyrido[l,2-u]pyr-imidine-3-carboxylates in a mixture of POCI3 and DMF at lower (20-25 °C) and higher (95 100°C) temperatures, respectively. 9-(Ethoxycarbonyl-methyl)-4-oxo-6,7-dihydro-47/-pyrido[l,2-a]pyrimidine-3-carboxylate 158 (but not 9-ethoxycarbonylmethylene-6,7,8,9-tetrahydro derivative 157) was also transformed into ethyl 9-(ethoxycarbonylmethyl)-7-(l-chloroethyl)-4-oxo-477-pyrido[l, 2-a]pyrimidine-3-carboxylate (99T10221). 

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