Synthesis and X-Ray Crystal Structure of Two Acridinedione Derivatives

Dalbir Kour,Rajni Kant,D. R. Patil,Vivek K. Gupta,M. B. Deshmukh

doi:10.1155/2014/914504

Dalbir Kour, Rajni Kant + Show 3 more

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https://doi.org/10.1155/2014/914504

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Abstract

The two acridinedione derivatives 1 [3,3,6,6-tetramethyl-9-(4-methoxyphenyl)-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione (C24H29NO3)] and 2 [3,3,6,6-tetramethyl-9-(4-methylphenyl)-3,4,6,7,9,10-hexa-hydro-2H,5H-acridine-1,8-dione (C24H29NO2)] were synthesized and their crystal structures were determined by direct methods. The asymmetric unit of compound 1 contains two independent molecules. The 1,4-dihydropyridine (DHP) ring adopts boat conformation in both 1 and 2. In 1 the dione rings exist in sofa conformation (for both the crystallographically independent molecules) while the corresponding rings in 2 adopt half chair and sofa conformations, respectively. The crystal packing is stabilized by intermolecular N–H⋯O and C–H⋯O interactions in compound 1 and N–H⋯O interactions in compound 2.

Highlights

A multicomponent reaction (MCR) provides powerful tool for the synthesis of complex molecules and drug like heterocycles and has great interest in diversity oriented synthesis
Acridinediones containing a 1,4-DHP nucleus are used as laser dyes with very high efficiencies of photo initiators [4, 5]
A latest literature review reveals that 1,4-DHP nucleus exhibits calcium channels blockers and antiaggregatory activity

Summary

Introduction

A multicomponent reaction (MCR) provides powerful tool for the synthesis of complex molecules and drug like heterocycles and has great interest in diversity oriented synthesis. MCRs are economic, selective, plain procedure and time and power saving with being ecofriendly in organic synthesis [1,2,3]. Acridinediones containing a 1,4-DHP nucleus are used as laser dyes with very high efficiencies of photo initiators [4, 5]. A latest literature review reveals that 1,4-DHP nucleus exhibits calcium channels blockers and antiaggregatory activity. In continuation of our ongoing work on multicomponent reaction derivatives and their crystal structure analyses [9, 10], we report the synthesis and crystal structure of 3,3,6,6-tetramethyl-9-(4-methoxyphenyl)-3,4,6,7,9,10 hexahydroacridine-1,8-dione 1 and 3,3,6,6-tetramethyl-9(4-methylphenyl)-3,4,6,7,9,10 hexahydroacridine-1,8-dione 2 (Scheme 1)

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