Tandem Synthesis and Optical Rotatory Dispersion Studies of a Novel Spiro Lactone (methyl 3-(benzo[d]thiazol-2-ylamino)-7,9-dimethyl-2,6,8,10-tetraoxo-1-oxa-7,9-diazaspiro[4.5]dec-3-ene-4-carboxylate)

Authors

  • Karim Ghafouri Department of Chemistry, Shahr-e-Qods Branch, Islamic Azad University, Tehran , Iran
  • Sajjad Sedaghat Department of Chemistry, Shahr-e-Qods Branch, Islamic Azad University, Tehran , Iran
  • Samira Arab-salmanabadi Department of Chemistry, Shahr-e-Qods Branch, Islamic Azad University, Tehran , Iran
Abstract:

Spiro compounds are of interest due to their interesting conformational features and their structural implications on biological systems. The asymmetric characteristic of the molecule due to the chiral spiro carbon is one of the important criteria of the biological activities. These structures are a widespread structural motif found as key elements of numerous drugs and designed medicinal agents in medicinal chemistry. Synthesis of these compounds always has been a challenging for organic chemists because it often requires synthetic design based on specific strategies. Due to the great importance of this class of compounds, chemists have a special attention to the synthesis of these compounds and a range of synthesis methods has been reported. In the current research a novel optically active spiro-lactone was synthesized via a tandem protocol ( michael addition, aldol reaction and γ-lactonization consecution) between benzo[d]thiazol-2-amine and dimethyl-acetylene dicarboxylate in the presence of 2, 4, 5, 6(1H, 3H)–pyrimidinetetrone (Alloxan). The synthesized compound has been successfully characterized by spectroscopy techniques. Also, evaluation of special optical rotatory on this synthesized spiro-lactone was investigated.  

Upgrade to premium to download articles

Sign up to access the full text

Already have an account?login

similar resources

1′-Methyl-2,2′′-dioxoindoline-3-spiro-2′-pyrrolidine-3′-spiro-3′′-indoline-4′,4′-di­carbonitrile

In the title compound, C(21)H(15)N(5)O(2), the pyrrolidine ring adopts a twist conformation. Both the oxindole rings are planar [maximum deviations of 0.076 (1) and 0.029 (1) Å in the two rings] and are oriented at a dihedral angle of 72.7 (1)°. The crystal structure is stabilized by C-H⋯O, N-H⋯O, N-H⋯N and C-H⋯π inter-actions.

full text

1′-Methyl-4′-(1-naphth­yl)-1′′,2′′,3′′,4′′-tetra­hydro­indane-2-spiro-2′-pyrrolidine-3′-spiro-2′′-naphthalene-1,3,1′′-trione

In the title compound, C(32)H(25)NO(3), the pyrrolidine ring adopts an envelope conformation, whereas the cyclo-hexa-none ring in the tetra-hydro-naphthalene fused-ring system adopts a half-chair conformation. The indanedione unit is oriented at an angle of 58.9 (1)° with respect to the naphthyl ring system. Three intra-molecular C-H⋯O close contacts and an intra-molecular C-H⋯π inter-action ar...

full text

STUDIES ON HYDRALAZINES - PART-1x1 PREPARATION AND ANTIMICROBIAL ACTIVITY OF 1 - (PHTHALAZIN- 1 '-YLAMINO)- 3-CHLORO-4-ARYL- 4H-(OR 4-METHYL)-2-AZETIDINONE

1- (Phthalazin-l'-yl-amino)-3-chloro-4-aryl-4H-(4o-rm ethyl)-2-azetidinones (3) were prepared by cycloaddition of-methyl substituted benzal hydrazinophthalazine (2) with chloro acetylchloride. The hydrazone (2) was synthesised by the condensation of 1- hydrazinophthalazine (1) with substituted aromatic aldehydes, ketones 7 acetophenones. 1- Hydrazinophthalazine was prepared from the phthal...

full text

5′′-(4-Chloro­benzyl­idene)-1′,1′′-dimethyl-3′-phenyl­acenaphthene-1-spiro-2′-pyrrolidine-3′-spiro-3′′-pyridine-2,4′′-dione

In the title compound, C(34)H(28)Cl(2)N(2)O(2), the five-membered pyrrolidine ring adopts an envelope conformation and the six-membered piperidinone ring is in a distorted half-chair conformation. The mol-ecular structure shows three intra-molecular C-H⋯O inter-actions and the crystal packing is stabilized through inter-molecular C-H⋯O and C-H⋯π inter-actions.

full text

Crystal and Molecular Structure Studies of Ethyl 4-(4-Hydroxyphenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene-1-carboxylate and Ethyl 4-(3-Bromophenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene-1-carboxylate

The crystal and molecular structures of the title compounds, ethyl 4-(4-hydroxyphenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene-1-carboxylate (I) and ethyl 4-(3-bromophenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene-1-carboxylate (II), are reported and confirmed by single crystal X-ray diffraction data. Compound (I), C26H24O5, crystallizes from a methanol solution in the monoclinic C2/c ...

full text

1′-Benzyl-4,4′′-bis­(4-chloro­phen­yl)-3-(2,6-dichloro­phen­yl)-1′′-methyl-4,5-dihydro­isoxazole-5-spiro-3′-piperidine-5′-spiro-3′′-pyrrolidine-2′′-spiro-3′′′-indoline-2′′′,4′-dione

The asymmetric unit of the title compound, C(43)H(34)Cl(4)N(4)O(3), contains two crystallographically independent mol-ecules. In both mol-ecules, the pyrrolidine ring adopts a twist conformation, the oxindole units are slightly distorted from planarity and the isoxazoline ring adopts an envelope conformation. The crystal structure is stabilized by N-H⋯O hydrogen-bonding inter-actions giving one...

full text

My Resources

Save resource for easier access later

Save to my library Already added to my library

{@ msg_add @}


Journal title

volume 7  issue 3

pages  1- 12

publication date 2017-08-01

By following a journal you will be notified via email when a new issue of this journal is published.

Hosted on Doprax cloud platform doprax.com

copyright © 2015-2023