Novel formation of 9,18-diformyl-5,6,14,17-tetrahydro-8,17-epoxy-6H,15H-[1,5] diazocino[2,1,-a: 6,5-a′]diisoquinolines from (3,4-dihydroisoquinolinyl-1) propan-1,3-dials

Nagarajan, K.; Rodrigues, Patrick J.; Go, K.; Parthasarathy, R.

doi:10.1016/s0040-4039(00)61113-9

Cited by 6 publications

(3 citation statements)

References 2 publications

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“…Nagarajan et al . observed that the treatment of aminomethylenemalonaldehyde 4 with acetic anhydride gives the O‐bridged diazocine 5 (Scheme ) . A similar self‐dimerization was also reported for substituted o ‐aminobenzaldehyde .…”

Section: Methodssupporting

confidence: 64%

Indole‐Fused Epoxy‐1,5‐Diazocines as Cancer‐Selective Cytotoxic Agents

Faraj

Khaledi

Karimian

et al. 2016

Journal of Heterocyclic Chem

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Dimerization of 2‐(diformylmethylene)‐3,3‐dimethylindole by the action of tosyl chloride (TsCl) led to the creation of an epoxy‐[1,5]‐diazocine bicycle. The structure of the molecule resembles that of the naturally occurring C‐curarine‐I. The molecule shows significant cytotoxicity against cancer lines MCF‐7 and MDA‐MB‐231, but not toward the normal cell line CCD‐841. A series of substituted 2‐(diformylmethylene)‐3,3‐dimethylindoles was accordingly dimerized, and the products were studied for their cytotoxic activities.

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Section: Methodssupporting

confidence: 64%

Indole‐Fused Epoxy‐1,5‐Diazocines as Cancer‐Selective Cytotoxic Agents

Faraj

Khaledi

Karimian

et al. 2016

Journal of Heterocyclic Chem

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“…Analytical and spectral data as well as single-crystal X-ray studies by Dr R Parthasarathy were provided in favour of 81. 59 This again is a general reaction of the analogues of 79.…”

Section: Villsmeyer-haack (Vh) Reaction Products From 1-methyl-34-dimentioning

confidence: 95%

Creative research in the chemical industry – Four decades in retrospect

Nagarajan¹

2006

J Chem Sci

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My professional research career spanning more than four decades has been largely devoted to synthetic medicinal chemistry (Ciba, Bombay-now Mumbai-21 years) followed by an equal number of years in process development of drugs, crop protection chemicals (Searle, Bombay) and drugs and speciality chemicals (Recon and Hikal, Bangalore). These efforts have involved several collaborators including many from other institutions and offered multitudinous challenges calling for continuous creativity in industrial setups. I was fortunate to have had a conducive environment to be able to respond to these challenges. I attempt to offer the readers in the ensuing pages a flavour of the excitement that has marked these years.

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“…It should be noted that thermal decomposition gave mainly aldehydes, without subsequent auto-condensation. In their search for applications of vicinal dialdehydes for the synthesis of isoquinolines, Nagarajan and co-workers 21 showed that acylation of isoquinoline derivatives 14 does not lead to the desired N-acylated heterocycles, but instead epoxy [1,5][b,f]diazocines 15 are formed as the major products (Scheme 4). Unfortunately, these structurally complex heterocycles are isolated in low yields (15a-d, 9-28%).…”

Section: Short Review Synthesismentioning

confidence: 99%

Epoxydibenzo[b,f][1,5]diazocines: From a Hidden Structural Motif to an Efficient Solvent-Free Synthetic Protocol

Michalak¹,

Depa²,

Bisek³

et al. 2022

Synthesis

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Epoxydiazocines belong to the rare class of small V-shaped molecules, closely related to Tröger’s base. Due to their intriguing, unique structure, they could serve as molecular building blocks for supramolecular chemistry. An extensive review on their synthesis is contained in this article. Moreover, our recent findings devoted to efficient and easily scalable synthesis of fluorinated epoxy[1,5][b,f]diazocines through solvent-free base-catalyzed condensation of ortho-aminophenones is provided. The unique V-shaped structure was confirmed by X-ray crystal structure analysis. Furthermore, the rigidity of the epoxydiazocine skeleton allowed for racemate separation and the configuration of enantiomers was established by combining quantum chemical calculations and chiroptical methods.1 Introduction2 Synthetic Efforts Towards Epoxydibenzo[b,f][1,5]diazocines3 Synthetic Efforts Towards Fluorinated Epoxydibenzo[b,f][1,5]diazocines4 Conclusion

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Novel formation of 9,18-diformyl-5,6,14,17-tetrahydro-8,17-epoxy-6H,15H-[1,5] diazocino[2,1,-a: 6,5-a′]diisoquinolines from (3,4-dihydroisoquinolinyl-1) propan-1,3-dials

Cited by 6 publications

References 2 publications

Indole‐Fused Epoxy‐1,5‐Diazocines as Cancer‐Selective Cytotoxic Agents

Indole‐Fused Epoxy‐1,5‐Diazocines as Cancer‐Selective Cytotoxic Agents

Creative research in the chemical industry – Four decades in retrospect

Epoxydibenzo[b,f][1,5]diazocines: From a Hidden Structural Motif to an Efficient Solvent-Free Synthetic Protocol

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