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

Abstract

N,N,N',N'‐tetrabromobenzene‐1,3‐disulfonamide and poly(N,N’‐dibromo‐N‐ethyl‐benzene‐1,3‐disulfonamide) were used as efficient catalysts for one‐pot synthesis of new quinazoline derivatives from various aldehydes, 2‐amino‐benzophenone, and ammonium acetate in good to excellent yields and new benzopyrano[2,3‐d]pyrimidine derivatives from salicylic aldehydes, various cyclic amines, and malononitrile in good to high yields.

Synthesis of Quinazoline Derivatives Catalyzed by a New Efficient Reusable Nanomagnetic Catalyst Supported with Functionalized Piperidinium Benzene‐1,3‐Disulfonate Ionic Liquid

“…At this stage, we speculate that the intermediate 3 reacts with the ammonium acetate to form intermediate 4 . Finally, it was observed that cyclization and aromatization of intermediate 5 results in the final product 6 (Scheme ) …”

“…For this purpose, some routes have been already reported that we review them here. Three‐component reaction catalyzed by polyphosphate ethyl ester (PPE), palladium, TBBDA, copper 1‐methylimidazolium triflouroacetate ([Hmim]TFA), butylmethylimidazolium tetrachloroferrate (bmim[FeCl 4 ]), Fe 3 O 4 /SBA‐15, CoFe 2 O 4 @B 2 O 3 ‐SiO 2 , Fe 3 O 4 @SiO 2 @TiO 2 ‐OSO 3 H, and acetic acid provide the synthesis of various quinazoline and dihydroquinazolinone derivatives. The methods reviewed above have some disadvantages such as long reaction times, by products, low product efficiency and expensive or poisonous catalysts.…”

An efficient CuO/rGO/TiO2photocatalyst for the synthesis of benzopyranopyrimidine compounds under visible light irradiation

“…26 The anti-coagulant and anti-HIV, 27 anti-histaminic, anti-microbial, 28 anti-cancer and anti-tuberculosis 29 activities of benzopyranes have been demonstrated. The presence of two backbones of pyrimidines and benzopyran in benzopyranopyrimidines has induced biological properties such as anti-inflammatory and analgesic 30 to this group of compounds. Benzopyrano[2,3- d ]pyrimidines were developed by O'Callaghan from the condensation reaction of 2-iminocoumarin-3-carboxamide with aldehydes.…”

One-Pot Synthesis of Quinazoline Derivatives Using Copper Nanocatalyst Stabilized on Graphene Oxide Functionalized by N1,N2-bis((Pyridine-2-yl)Methyl)Benzene-1,2-Diamine

“…Furthermore, the application and frequent presence of structure of qunazoline in immensely important drugs such as Prazosin, Gefitinib and Erlotinib that they are used as an anticancer drug (Figure 2) has led scientists to call this structure pharmaceutical skeleton. As a matter of fact, choosing this name describes the importance of its synthesis [1][2][3][4][5][6][7][8][9][10]. The fact that presence of catalyst in chemical reaction is important is obvious to all.…”

“…In recent years, different strategies have been proposed for the synthesis of quinazoline. In 2015, Ghorbani-Vaghei et al the quinazoline derivatives were synthesized using TBBDA and PBBS catalysts[8]. Deshmukh et al in 2018 were able to synthesize quinazoline derivatives using benzylamine, ammonium acetate and 2-aminobenzylalcohol[2].…”