Synthesis of Novel Tetrazole Containing Quinoline and 2,3,4,9‐Tetrahydro‐1 H ‐β‐Carboline Derivatives

A double four component Azido‐Ugi reaction of isocyanide, TMSN3, aldehyde, and 4,4′‐sulfonyldianiline with two amine functional groups in MeOH at 65°C has been described. The synthesis of pharmacologically and structurally interesting compounds with two 1,5‐disubstituted tetrazole rings via a reaction from available and inexpensive reagents under a convenient process and mild reaction conditions has been reported. Modifications in the structure of the reaction product could be followed by varying the aldehyde or isocyanide component. The products are new and were well described by Mass, 1H NMR, and 13C NMR spectral studies.

Section: Introductionmentioning

confidence: 99%

Synthesis of bis(1,5‐disubstituted tetrazoles) via double four component Azido‐Ugi reaction

Dehghan

Nasr‐Isfahani

Sarvary

et al. 2020

“…To the best of our knowledge, there is no report on the preparation of bis‐heterocycles containing a carbazole core linked with 1,5‐DS‐1 H ‐T cycles through MCRs. Therefore, based on the documented pharmacological potential of these two building blocks, and our interest in the synthesis of tetrazole derivatives using the isocyanide‐based multicomponent reactions (IMCRs), [ 39–42 ] here we describe the synthesis of novel symmetrical analogs of 1,5‐DS‐1 H ‐T‐containing carbazole derivatives via the Ugi‐azide reaction of 3,6‐diformyl‐9‐alkylcarbazoles, aromatic amines, isocyanides, and trimethylsilyl azide (TMSN 3 ) in methanol.…”

Section: Introductionmentioning

confidence: 99%

Preparation of novel symmetrical bistetrazole‐carbazole derivatives through a one‐pot Ugi‐azide reaction

Rahimi

Ghandi

2020

Self Cite

A series of new symmetrical tetrazole‐based carbazole derivatives starting from the initially generated 3,6‐diformyl‐N‐alkylcarbazoles were successfully synthesized through a one‐pot Ugi‐azide reaction in moderate to high yields. Simplicity, easily accessible chemicals, mild reaction conditions, and fast separation of the products with the formation of bistetrazole‐based carbazole derivatives in one step are some advantages of this method. The structure of the products was characterized and confirmed by using spectroscopic techniques such as 1H NMR, 13C NMR, FT‐IR, and MS spectroscopy.

“…One‐pot multicomponent reactions are one of the best strategies for diversity‐oriented synthesis (DOS) of biological active compounds . In comparison with multistep synthetic procedures, multicomponent reactions are simple, fast, and highly economical manner to construction of varyingly substituted molecules in just one reactor by avoiding separation and purification of intermediates .…”

Section: Introductionmentioning

confidence: 99%

Two Different Green Catalytic Systems for One‐Pot Regioselective and Chemoselective Synthesis of Some Pyrimido[4,5‐d]Pyrimidinone Derivatives in Water

Rimaz

Khalafy

Mousavi

et al. 2017

In this work, we have developed green and efficient regioselective and chemoselective syntheses of 5‐aryloyl‐1,3‐dimethyl‐7‐thioxo‐5,6,7,8‐tetrahydropyrimido[4,5‐d]pyrimidine‐2,4(1H,3H)‐dione and 5‐aryloyl‐1,3‐dimethyl‐2,7‐dithioxo‐2,3,5,6,7,8‐hexahydropyrimido[4,5‐d]pyrimidin‐4(1H)‐one derivatives via one‐pot three‐component Biginelli‐like condensation of arylglyoxal monohydrates, N,N‐dimethylbarbituric acid or N,N‐dimethyl‐2‐thiobarbituric acid, and thiourea in water at 50°C. The presence of two different green catalytic systems (ZrOCl2.8H2O and also DABCO) proceeded efficiently to afford the desired products in good‐to‐excellent yields. An aqueous reaction medium, high regioselectivity and chemoselectivity, simple operation and suitable yields of products are the important features of these green protocols.