Parallel Solution-Phase Synthesis of (Z)-3-(Arylamino)-2,3-dehydroalanine Derivatives and Solid-Phase Synthesis of Fused Pyrimidones

Abstract

N-Protected (Z)-3-(arylamino)-2,3-dehydroalanine esters 5 and 10 were prepared in one step from methyl (Z)-2-acylamino-3-(dimethylamino)prop-2-enoates 3 and 9 and anilines 4 employing a parallel solution-phase synthetic approach. In most cases, analytically pure products 5 and 10 were obtained. On the other hand, a three-step parallel solid-phase synthesis of 2-acetylamino-4H-azino[1,2-x]pyrimidin-4-ones 15 via the polymer-bound methyl (Z)-2-acetylamino-3-(dimethylamino)prop-2-enoate (12) was also developed.

Synthesis and antimycobacterial activity of alkyl 1-heteroaryl-1H-1,2,3-triazole-4-carboxylates

“…A growing problem also is HIV-infected patients, which are particularly vulnerable to turn infection with M. tuberculosis into active TB [1].In the last two decades, a series of 2-substituted alkyl 3-(dimethylamino)prop-2-enoates and related enaminones were prepared and used as versatile reagents for the preparation of various heterocyclic systems, functionalised heterocyclic compounds, and natural product analogues [2][3][4][5][6][7]. Just recently, the enaminone methodology has been employed in combinatorial synthesis [8][9][10]. The use of 2acylamino and 2-vinylamino substituted alkyl 3-(dimethylamino)propenoates also offers an easy access to various 3-amino-4H-quinolizin-4-ones and 3-amino substituted fused pyrimidones, which can be transformed into the corresponding diazonium tetrafluoroborates as versatile intermediates for further transformations [11][12][13][14][15].…”

Fast, Microwave-Promoted One-Pot Synthesis of Bicyclic Pyrimidones from Baylis-Hillman Adducts

“…[16][17][18][19][20] However, most of these methods suffered from some drawbacks including difficultly accessible starting materials or the requirement for multistep synthetic transformations.…”

“…Several approaches for the synthesis of 4H-pyrimido [1,2-b] pyridazin-4-ones 3 have been described in the literature, [16][17][18][19][20][21][22][23][24] and the classical method for the synthesis of 4H-pyrimido [1,2-b] pyridazin-4-ones, proposed by Svete and his co-workers, was by treatment of appropriately substituted 3-(dimethylamino) prop-2-enoates and 3-aminopyridazines in acetic acid. [16][17][18][19][20] However, most of these methods suffered from some drawbacks including difficultly accessible starting materials or the requirement for multistep synthetic transformations.…”

A simple synthesis of 4-aroyl-5-methyl-1H-imidazol-2(3H)-one derivatives (Enoxymone analogues) from aryl methyl ketones via enaminones

“…The wide applicability of 3-(dimethylamino)-propenoates and related enaminones as versatile reagents in heterocyclic synthesis, 21 parallel solution-phase and solid-phase synthesis of fused pyrimidinones, 22 and stereochemical synthesis, 23 including natural products and their analogues, e.g. the aplysinopsins, 24 meridianines, 25 dipodazines, 26 and triprostatines 27 has been demonstrated.…”