Solvent-free synthesis of triazines using N-halosulfonamides

Abstract

We have developed an efficient procedure for the synthesis of 1,2,4-triazine derivatives using [TBBDA] and [PBBS] as new catalysts.

Facile and efficient approach for the synthesis of spirocyclopropylbarbiturates and 3-substituted-1,1,2,2-tetracyanocyclopropanes using N-halosulfonamides

“…Based on the above facts and in continuation of our previous studies on the application of N -halo reagents in organic synthesis [27][28][29][30], we now report convenient methods for the cyclopropanation of 2-arylidenemalononitriles 1 with barbituric acids 2 and cyclopropanation of carbonyl The reaction of benzylidenemalononitrile 1g as a model compound with barbituric acid 2 was examined under various reaction conditions (Table 1). First, the effect of various bases was investigated (Table 1, entries 1-7).…”

N,N,N′,N′‐Tetrabromobenzene‐1,3‐disulfonamide Catalyzed Synthesis of New Spiro[chroman‐3,2′‐chromeno[2,3‐b]furan]‐2,4,4′‐(3′H)‐trione Derivatives

“…In continuation of our interest in the application of N,N, N′,N′-tetrabromobenzene-1,3-disulfonamide (TBBDA) in organic synthesis [24][25][26][27][28][29][30][31][32], herein, we report a simple and efficient process for synthesis of new spiro dihydrofuranfused coumarin framework via tandem reaction of 4-hydroxycoumarin with aromatic and heteroaromatic aldehydes in the presence of TBBDA and pyridine at room temperature in good to high yields under solventfree conditions (Scheme 1).…”

“…Probable reaction mechanism in this way that TBBDA release Br + in situ, which can act as an electrophilic species [31], therefore, the activation of aldehyde with Br + subsequently enhanced condensation reaction 1 with 2 and Michael addition of 4-hydroxycumarin 4 with 3 to afford intermediate 5. After tutomerization and interamolecular nucleophilic addition of 6 spiro [chroman-3,2′-chromeno[2,3-b]furan]-2,4,4′-(3′H)-trione, derivatives were produced [20].…”

Efficient One‐Pot Synthesis of Quinazoline and Benzopyrano[2,3‐d]pyrimidine Derivatives Catalyzed by N‐Bromosulfonamides

“…As a part of our research in organic synthesis catalyzed by N,N,N',N'-tetrabromobenzene-1,3-disulfonamide (TBBDA) and poly(N,N'-dibromo-N-ethyl-benzene-1,3-disulfonamide) (PBBS) [18][19][20][21][22][23][24][25][26][27], hereby, we report simple, green, and efficient method for synthesis of quinazoline derivatives via one-pot, three-component reaction of substituted o-aminoaryl ketones, various aldehydes and ammonium acetate in ethanol and synthesis of benzopyrano[2,3-d]pyrimidine derivatives from salicylic aldehydes, malononitrile, and various cyclic amines via one-pot and pseudo four-component reaction in the presence of TBBDA or PBBS as catalysts under mild conditions (Scheme 1).…”