Document Detail


Synthesis of indan-based unusual alpha-amino acid derivatives under phase-transfer catalysis conditions.
MedLine Citation:
PMID:  10814097     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Conformationally constrained cyclic alpha-amino acid derivatives were synthesized under solid-liquid phase-transfer catalysis conditions. This methodology involves the bis-alkylation of ethyl isocyanoacetate with various alpha,alpha'-dibromo-o-xylene derivatives [alpha,alpha'-dibromo-o-xylene 5, 2,3-bis(bromomethyl)-1, 4-dimethoxybenzene 6, 1,2-bis(bromomethyl)-4,5-dibromobenzene 7, 2, 3-bis(bromomethyl)naphthalene 8, 1,8-bis(bromomethyl)-naphthalene 9, 6,7-bis(bromomethyl)-2,2-dimethyl-1H-phenalene-1,3(2H)-dione 10, 2, 3-bis(bromomethyl)-1,4-anthraquinone 11, 6, 7-bis(bromomethyl)quinoxaline 12, 3,4-bis(bromomethyl)furan 13, 1,2, 4,5-tetrakis(bromomethyl)benzene 28, and hexakis(bromomethyl)benzene 30] using potassium carbonate as a base and tetrabutylammonium hydrogensulfate as a phase-transfer catalyst to give corresponding isonitrile derivatives, which upon hydrolysis with HCl in ethanol gave amino esters. Using this method electron-deficient as well as electron-rich and halogen-substituted indan-based alpha-amino acids were prepared. The preparation of bis-indan as well as tris-indan alpha-amino esters is also described.
Authors:
S Kotha; E Brahmachary
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  65     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2000 Mar 
Date Detail:
Created Date:  2000-10-27     Completed Date:  2000-10-27     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  1359-65     Citation Subset:  IM    
Affiliation:
Department of Chemistry, Indian Institute of Technology, Powai, Mumbai 400 076, India.
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MeSH Terms
Descriptor/Qualifier:
Acetic Acids / chemistry,  metabolism
Alkylation
Amino Acids / chemical synthesis*,  chemistry
Catalysis
Esters / chemical synthesis,  chemistry
Hydrolysis
Indans / chemical synthesis*,  chemistry
Magnetic Resonance Spectroscopy
Molecular Conformation
Peptides / chemistry
Chemical
Reg. No./Substance:
0/Acetic Acids; 0/Amino Acids; 0/Esters; 0/Indans; 0/Peptides; 105-56-6/ethyl cyanoacetate

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