Synthesis of New Imino Containing Tetrahydrochromeno[2,3‐d]pyrimidines

Abstract

Some new derivatives of 3,5‐diaryl‐4‐imino‐5,7,8,9‐tetrahydro‐3H‐chromeno[2,3‐d]pyrimidine have been prepared through a condensation reaction of 2‐amino‐4‐aryl‐3‐cyano‐5,6,7,8‐tetrahydrobenzo[b]pyrans with triethyl orthoformate in boiling acetic anhydride followed by cyclization with primary aryl amines in the presence of a few drops triethylamine as catalyst in refluxing ethanol. The products were characterized on the basis of IR, 1H‐NMR, and 13C‐NMR spectral and microanalytical data.

Facile Synthesis of New 6‐Alkylamino‐1H‐pyrazolo[3,4‐b]pyridine‐5‐carbonitrile Derivatives

“…Taking all these facts into consideration, and in conjunction with our earlier studies of synthesis of heterocyclic compounds , herein, we report the synthesis of some new derivatives of 6‐alkylamino‐1,3‐diphenyl‐1 H ‐pyrazolo[3,4‐ b ]pyridine‐5‐carbonitrile 4a–f in synthetically useful yields by Knoevenagel condensation of 5‐chloro‐1,3‐diphenyl‐1 H ‐pyrazole‐4‐carbaldehyde 1 with malononitrile 2 in ethanol containing a few drops of glacial acetic acid at reflux temperature, which afforded compound 3 , followed by cyclization with primary alkyl amines in the presence of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) as catalyst in refluxing ethanol (Scheme ). To the authors' knowledge, compounds 4a–f are new and have not been reported in the literature.…”

Triethylamine — A Versatile Organocatalyst in Organic Transformations: A Decade Update

“…197 There are some reports [198][199][200] in the literature on the synthetic drives of such biologically promising heterocyclic scaffolds. Davoodina and co-workers 201…”

The link between relative stability constant of DNA- and BSA-chromenopyrimidine complexes and cytotoxicity towards human breast cancer cells (MCF-7)

“…They are oen synthesized by multicomponent reactions which enable the desired products to be isolated in a few steps via a single-pot operation. [14][15][16][17][18][19][20] Chromenopyrimidine derivatives have been reported to be light emitters which can be ne-tuned by varying the substituents on the chromenopyrimidine core. 14 This the class compounds as potential emitters in optoelectronic devices such as organic light-emitting diodes (OLEDs).…”