Synthesis of annulated pyrroles: Condensation of aldose sugars, arylamines, and 1,3-diones using TBAB

Synthesis

Volumn , Issue 19, 2010, Pages 3374-3378

  Nagarapu, Lingaiah ^a   Cheemalapati, Venkata Narasimhaji ^a   Karnakanti, Shuklachary ^a   Bantu, Rajashaker ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

1,3 diones; aldose sugars; one pot synthesis; shorter reaction times; tetrabutylammonium bromide

Indexed keywords

1,3-DIONES; ALDOSE SUGARS; ONE-POT SYNTHESIS; REACTION TIME; TETRABUTYLAMMONIUM BROMIDE;

ACETYLATION; BROMINE COMPOUNDS; KETONES; POTASSIUM COMPOUNDS; SUGAR (SUCROSE);

SYNTHESIS (CHEMICAL);

3 ACETYL 6 ACETOXY 2 METHYL 1 PHENYL 1,4,5,6 TETRAHYDROPYRANO[3,2 B]PYRROLE; 6 ACETOXY 5 (ACETOXYMETHYL) 3 ACETYL 1 (2,6 DIMETHYLPHENYL) 2 METHYL 1,4,5,6 TETRAHYDROPYRANO[3,2 B]PYRROLE; 6 ACETOXY 5 (ACETOXYMETHYL) 3 ACETYL 1 (4 FLUOROPHENYL) 2 METHYL 1,4,5,6 TETRAHYDROPYRANO[3,2 B]PYRROLE; 6 ACETOXY 5 (ACETOXYMETHYL) 3 ACETYL 1 (4 ISOPROPYLPHENYL) 2 METHYL 1,4,5,6 TETRAHYDROPYRANO[3,2 B]PYRROLE; 6 ACETOXY 5 (ACETOXYMETHYL) 3 ACETYL 2 METHYL 1 (2 METHYLPHENYL) 1,4,5,6 TETRAHYDROPYRANO[3,2 B]PYRROLE; 6 ACETOXY 5 (ACETOXYMETHYL) 3 ACETYL 2 METHYL 1 [4 (TRIFLUOROMETHOXY)PHENYL] 1,4,5,6 TETRAHYDROPYRANO[3,2 B]PYRROLE; 6 ACETOXY 5 (ACETOXYMETHYL) 3 ACETYL 2 METHYL 1 PHENYL 1,4,5,6 TETRAHYDROPYRANO[3,2 B]PYRROLE; AROMATIC AMINE; CARBOHYDRATE DERIVATIVE; ETHYL 6 ACETOXY 5 (ACETOXYMETHYL) 1 (2,6 DIMETHYLPHENYL) 2 METHYL 1,4,5,6 TETRAHYDROPYRANO[3,2 B]PYRROLE 3 CARBOXYLATE; ETHYL 6 ACETOXY 5 (ACETOXYMETHYL) 1 (4 ISOPROPYLPHENYL) 2 METHYL 1,4,5,6 TETRAHYDROPYRANO[3,2 B]PYRROLE 3 CARBOXYLATE; ETHYL 6 ACETOXY 5 (ACETOXYMETHYL) 2 METHYL 1 (2 METHYLPHENYL) 1,4,5,6 TETRAHYDROPYRANO[3,2 B]PYRROLE 3 CARBOXYLATE; ETHYL 6 ACETOXY 5 (ACETOXYMETHYL) 2 METHYL 1 (4 FLUOROPHENYL) 1,4,5,6 TETRAHYDROPYRANO[3,2 B]PYRROLE 3 CARBOXYLATE; ETHYL 6 ACETOXY 5 (ACETOXYMETHYL) 2 METHYL 1 [4 (TRIFLUOROMETHOXY)PHENYL] 1,4,5,6 TETRAHYDROPYRANO[3,2 B]PYRROLE 3 CARBOXYLATE; ETHYL 6 ACETOXY 5 (ACETOXYMETHYL) 2 METHYL 1 PHENYL 1,4,5,6 TETRAHYDROPYRANO[3,2 B]PYRROLE 3 CARBOXYLATE; KETONE DERIVATIVE; PYRROLE DERIVATIVE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CATALYSIS; DRUG SYNTHESIS; POLYMERIZATION; REACTION TIME;

EID: 77957143601     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1257973     Document Type: Article

References (15)

1. Lin P, Lee C L., Sim M M., J. Org. Chem. 2001 66 6734
2. Hanessian S, Total Synthesis of Natural Products: The Chiron Approach Pergamon Oxford 1983
3. Fraser-Reid B, Anderson R C., Fortschr. Chem. Org. Naturst. 1980 39 1
4. Yadav J S., SubbaReddy B V., Srinivas M, Divyavani C, Basha S J., Sarma A V. S., J. Org. Chem. 2008 73 3252
5. Smietana M, Mioskowski C, Org. Lett. 2001 3 1037
6. Amantini C, Fringuelli F, Pizzo F, Vaccaro L, J. Org. Chem. 2001 66 6734
7. Selvakumar K, Zapt A, Beller M, Org. Lett. 2002 4 3031
8. Ranu B C., Dey S S., Hajra A, Tetrahedron 2003 59 2417
9. Ranu B C., Das A, Samanta S, J. Chem. Soc., Perkin Trans. 1 2002 1520
10. Kantevari S, Chary M V., Das A P. R., Srinivas V N. V., Lingaiah N, Catal. Commun. 2008 9 2013
11. Amantini D, Fringuelli F, Pizzo F, Vaccaro L, J. Org. Chem. 2001 66 6734
12. Kantevari S, Chary M V., Das A P. R., Srinivas V N. V., Lingaiah N, Catal. Commun. 2008 9 1575
13. Nagarapu L, Chary M V., Supriya B, Satyender A, Rajashaker B, Synthesis 2009 2279
14. Nagarapu L, Gopal P, Satyender A, Synth. Commun. 2009 39 355
15. Nagarapu L, Bantu R, Mereyala H. B, J. Heterocycl. Chem. 2009 46 728