Recent advances in the chemistry of thieno[2,3-b]pyridines 1. Methods of synthesis of thieno[2,3-b]pyridines

Abstract

Recent advances in the chemistry of thieno[2,3-b]pyridines 1. Methods of synthesis of thieno[2,3-b]pyridines*

Synthesis and Analgesic Activity of New Heterocyclic Cyanothioacetamide Derivatives

“…One of the main directions of the use of thioamide 1 is the preparation of a wide range of S,Nheterocyclic compounds, the most important of which are 3-cyanopyridine-2(1H)-thiones 2 [5][6][7][8][9][10][11] (Scheme 1). Compounds 2 are a convenient scaffolds for the synthesis of a wide range of thieno [2,3-b]pyridines [12][13][14][15][16][17][18][19][20], thiazolo [3,2-a]pyridines [21][22][23][24][25][26][27][28][29], pyrido [2,1-b] [1,3,5]thiadiazines [30 -34], dipyrido[1,2-a:1'2'-e] [1,3,5,7]tetrazocines [35], pyrido [1,2-a] [1,3,5] triazines [36], isothiazolo [5,4-b]pyridines [37][38][39][40], and other bi-and polycyclic structures.…”

Reactions of Malononitrile Dimer with Isothiocyanates

“…Continuing research on the chemistry of malononitrile dimer [10][11][12], we decided to study in detail the regioselectivity of the heterocyclization of 2-amino-1,1,3tricyanopropene 1 with isothiocyanates and establish the real structure of the resulting compounds. Possible products 2 hold promise as starting reagents for the synthesis of thieno [2,3-b]pyridine derivatives, many of which have pharmacologically useful properties [13][14][15][16]. On the other hand, compounds 2-4 are convenient and accessible substrates for preparing S, N-polyheterocyclic assemblies by the Mannich reaction (see, for example, [17][18][19][20][21]).…”

Synthesis and Some Properties of New 5-Hydroxy-2-[(hetarylthio)methyl]-4H-pyran-4-ones

“…In general, the analysis of literature data allows us to conclude that the reaction of halokojic acids with heterocyclic S-nucleophiles has been relatively little studied. For example, the reaction of 5-hydroxy-2-chloromethyl-4H-pyran-4-one with available 3-cyanopyridine-2(1H)-thiones and tautomeric mercaptans (for review works, see [47][48][49][50][51][52][53][54]) widely used in heterocyclic synthesis have not been reported earlier.…”