Type: Article

One-pot synthesis of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine and malonamide derivatives using multi-component reactions

Journal: Tetrahedron (00404020)Year: 2014/12/09Volume: 70Issue: 50Pages: 9512 - 9521

Rahmati A.^a Ahmadi S. Ahmadi-Varzaneh M.

a :University of Isfahan - IRAN(IR) - Isfahan

DOI:10.1016/j.tet.2014.10.060Language: English

Abstract

In this work, a new series of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine and malonamide derivatives have been synthesized using an aromatic 1,2-diamine, Meldrum's acid, an isocyanide, and an arylidene malononitrile (or an aldehyde and malononitrile instead of an arylidene malononitrile) in CH2Cl2 at ambient temperature. Synthesis of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine proceeded via four- and five-component reactions; while the synthesis of malonamide derivatives was performed using five- and six-component reactions. In addition, a new series of the malonamide derivatives have been prepared using an aldehyde, malononitrile, Meldrum's acid, an isocyanide, and two molecules of 1,4-diamine via a six-component reaction. These procedures provide alternative methods to the synthesis of a new series of 1,2,4,5-tetrahydro-2,4-dioxobenzo[b][1,4]diazepine and malonamide derivatives. © 2014 Elsevier Ltd. All rights reserved.

Author Keywords

DiazepinesMalonamidesMulti-component condensation reaction

Other Keywords

2 [1 (2,4 dichlorophenyl) 2 (cyclohexylamino) 2 (1,2,4,5 tetrahydro 2,4 dioxobenzo[b][1,4]diazepin 3 ylidene)ethyl]malononitrile2 [1,4 (chlorophenyl) 2 (cyclohexylamino) 2 (1,2,4,5 tetrahydro 2,4 dioxobenzo[b][1,4]diazepin 3 ylidene)ethyl]malononitrile2 [2 (2,4,4 trimethylpentan 2 ylamino) 1 (4 chlorophenyl) 2 (1,2,4,5 tetrahydro 2,4 dioxobenzo[b][1,4]diazepin 3 ylidene)ethyl]malononitrile2 [2 (cyclohexylamino) 2 (1,2,4,5 tetrahydro 2,4 dioxobenzo[b][1,4]diazepin 3 ylidene) 1 (2,4 dimethoxyphenyl)ethyl]malononitrile2 [2 (cyclohexylamino) 2 (1,2,4,5 tetrahydro 2,4 dioxobenzo[b][1,4]diazepin 3 ylidene) 1 (3,4 dimethoxyphenyl)ethyl]malononitrile2 [2 (cyclohexylamino) 2 (1,2,4,5 tetrahydro 2,4 dioxobenzo[b][1,4]diazepin 3 ylidene) 1 (4 nitrophenyl)ethyl]malononitrile2 [2 (cyclohexylamino) 2 (1,2,4,5 tetrahydro 2,4 dioxobenzo[b][1,4]diazepin 3 ylidene) 1 phenylethyl]malononitrile2 [2 (cyclohexylamino) 2 (1,2,4,5 tetrahydro 7 methyl 2,4 dioxobenzo[b][1,4]diazepin 3 ylidene) 1 phenylethyl]malononitrile2 [2 (tert butylamino) 2 (1,2,4,5 tetrahydro 2,4 dioxobenzo[b][1,4]diazepin 3 ylidene) 1 (4 chlorophenyl)ethyl]malononitrileamidebenzodiazepine derivativen 1, n 3 bis (2 amino 1,2 dicyanovinyl) 2 [1 (tert butylamino) 3,3 dicyano 2 (4 methoxyphenyl)propylidene]malonamiden 1, n 3 bis (2 amino 1,2 dicyanovinyl) 2 [3,3 dicyano 1 (cyclohexylamino) 2 (4 methoxyphenyl)propylidene]malonamiden 1, n 3 bis (2 amino 4,5 dichlorophenyl) 2 [2 (4 chlorophenyl) 3,3 dicyano 1 (cyclohexylamino)propylidene]malonamiden 1, n 3 bis (2 amino 4,5 dichlorophenyl) 2 [3,3 dicyano 1 (cyclohexylamino) 2 phenylpropylidene]malonamiden 1, n 3 bis (2 aminophenyl) 2 [3,3 dicyano 1 (cyclohexylamino) 2 phenylpropylidene]malonamiden,n bis (4 aminophenyl) 2 [1 (2,4,4 trimethylpentan 2 ylamino) 3,3 dicyano 2 (4 methoxyphenyl)propylidene]malonamiden,n bis (4 aminophenyl) 2 [1 (2,4,4 trimethylpentan 2 ylamino) 3,3 dicyano 2 (4 methylphenyl)propylidene]malonamiden,n bis (4 aminophenyl) 2 [1 (2,4,4 trimethylpentan 2 ylamino) 3,3 dicyano 2 (naphthalene 3 yl)propylidene]malonamiden,n bis (4 aminophenyl) 2 [1 (tert butylamino) 3,3 dicyano 2 (3 bromophenyl)propylidene]malonamiden,n bis (4 aminophenyl) 2 [1 (tert butylamino) 3,3 dicyano 2 (3,4 dimethoxyphenyl)propylidene]malonamiden,n bis (4 aminophenyl) 2 [1 (tert butylamino) 3,3 dicyano 2 (4 dimethylaminophenyl)propylidene]malonamiden,n bis (4 aminophenyl) 2 [1 (tert butylamino) 3,3 dicyano 2 (4 fluorophenyl)propylidene]malonamiden,n bis (4 aminophenyl) 2 [1 (tert butylamino) 3,3 dicyano 2 (4 methoxyphenyl)propylidene]malonamiden,n bis (4 aminophenyl) 2 [1 (tert butylamino) 3,3 dicyano 2 (naphthalene 3 yl)propylidene]malonamiden,n bis (4 aminophenyl) 2 [1 cyclohexylamino 3,3 dicyano 2 (3,4 dimethoxyphenyl)propylidene]malonamiden,n bis (4 aminophenyl) 2 [1 cyclohexylamino 3,3 dicyano 2 (4 diaminophenyl)propylidene]malonamiden,n bis (4 aminophenyl) 2 [1 cyclohexylamino 3,3 dicyano 2 (4 methoxyphenyl)propylidene]malonamiden,n bis (4 aminophenyl) 2 [1 cyclohexylamino 3,3 dicyano 2 (4 methylphenyl)propylidene]malonamiden,n bis (4 aminophenyl) 2 [1 cyclohexylamino 3,3 dicyano 2 (naphthalene 3 yl)propylidene]malonamideunclassified drugArticlechemical reactiondrug synthesiselectron transportenvironmental temperatureMichael additionmolecular weightmulticomponent reactionnucleophilicityone pot synthesispolymerizationpriority journalreaction timeroom temperaturetautomerization