+ Site Statistics
References:
52,572,879
Abstracts:
28,705,754
PMIDs:
27,750,366
DOIs:
25,464,004
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Acid-Catalyzed Multicomponent Tandem Double Cyclization: A One-pot, Metal-free Route to Synthesize Polyfunctional 4,9-Dihydropyrrolo[2,1-b]quinazolines



Acid-Catalyzed Multicomponent Tandem Double Cyclization: A One-pot, Metal-free Route to Synthesize Polyfunctional 4,9-Dihydropyrrolo[2,1-b]quinazolines



Journal of Organic Chemistry 81(17): 8104-8111



An acid-catalyzed multicomponent tandem double cyclization protocol has been developed for the synthesis of polyfunctional 4,9-dihydropyrrolo[2,1-b]quinazolines from simple and readily available arylglyoxal monohydrates, 2-aminobenzylamine, and trans-β-nitrostyrenes. This practical and metal-free reaction proceeds through an imine formation/cyclization/Michael addition/Henry cyclization protocol, resulting in the construction of four new bonds and two ring moieties directly in one pot.

Please choose payment method:






(PDF emailed within 0-6 h: $19.90)

Accession: 057123826

Download citation: RISBibTeXText

PMID: 27504693

DOI: 10.1021/acs.joc.6b01660


Related references

Acid-Catalyzed Multicomponent Tandem Cyclizations: Access to Polyfunctional Dihydroindolizino[8,7-b]indoles. Organic Letters 18(6): 1342-1345, 2016

An efficient route to synthesize isatins by metal-free, iodine-catalyzed sequential C(sp(3))-H oxidation and intramolecular C-N bond formation of 2'-aminoacetophenones. Organic & Biomolecular Chemistry 12(42): 8512-8518, 2015

Copper-catalyzed tandem Ullmann type C-N coupling and dehydrative cyclization: synthesis of imidazo[1,2-c]quinazolines. Organic & Biomolecular Chemistry 14(5): 1736-1741, 2016

Transition metal catalyzed radical cyclization new preparative route to gamma lactams from allylic alcohols via the 3.3 sigmatropic rearrangement of allylic trichloroacetimidates and the subsequent ruthenium catalyzed cyclization of n allyltrichloroacetamides. Journal of Organic Chemistry 57(6): 1682-1689, 1992

Ruthenium-catalyzed highly regioselective cyclization of ketoximes with alkynes by C-H bond activation: a practical route to synthesize substituted isoquinolines. Organic Letters 14(12): 3032-3035, 2012

Copper-catalyzed difunctionalization of activated alkynes by radical oxidation-tandem cyclization/dearomatization to synthesize 3-trifluoromethyl spiro[4.5]trienones. Chemistry 21(4): 1468-1473, 2015

Palladium-catalyzed tandem cyclization of 4,6- and 5,7-diendeamines A new route toward the pyrrolizidine and indolizidine alkaloids. Journal of the American Chemical Society 114(22): 8696-8698, 1992

A facile route to 2,4-dihydro-1H-benzo[d][1,3]thiazines via silver-catalyzed tandem addition-cyclization reactions. Journal of Combinatorial Chemistry 10(4): 541-545, 2008

Mechanisms of Metal-Free Aerobic Oxidation To Prepare Benzoxazole Catalyzed by Cyanide: A Direct Cyclization or Stepwise Oxidative Dehydrogenation and Cyclization?. Journal of Organic Chemistry 81(22): 10857-10862, 2016

A metal-free tandem C-C/C-O bond formation approach to densely functionalized indolyl 4H-chromenes catalyzed by polystyrene-supported p-toluenesulfonic acid under solvent-free conditions. Molecular Diversity 19(2): 367-383, 2016

Multicomponent Double Diels-Alder/Nazarov Tandem Cyclization of Symmetric Cross-Conjugated Diynones to Generate [6-5-6] Tricyclic Products. Chemistry 22(26): 8781-8785, 2016

Palladium-Catalyzed Ullmann Cross-Coupling/Tandem Reductive Cyclization Route to Key Members of the Uleine Alkaloid Family. Journal of Organic Chemistry 81(7): 2950-2957, 2016

FeCl 3 -Catalyzed Tandem Prins and Friedel-Crafts Cyclization: A Highly Diastereoselective Route to Polycyclic Ring Structures. Tetrahedron Letters 55(30): 4251-4254, 2014

ESI-MS studies on the mechanism of Pd0-catalyzed three-component tandem double addition-cyclization reaction. Journal of the American Chemical Society 127(37): 13060-4, 2005

A heavy metal- and oxidant-free, one-pot synthesis of pyridines and fused pyridines based on a Lewis acid-catalyzed multicomponent reaction. Chemical Communications 50(82): 12270-2, 2015