A facile multicomponent reaction involving isoquinoline, dimethyl allenedicarboxylate, and 2-oxo-1 h -indol-3-ylidenes

Synthesis

Volumn 44, Issue 3, 2012, Pages 417-422

  Rajan, Rejithamol ^a   Babu, Beneesh Pattoorpadi ^a   Kumar, Amit ^a   Paul, Rony Rajan ^a   Sinu, C R ^a   Suresh, Eringathodi ^b   Nair, Vijay ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

allenes; indoles; isoquinoline; multicomponent reactions; zwitterions

Indexed keywords

ALLENES; INDOLES; ISOQUINOLINES; MULTI-COMPONENT REACTIONS; ZWITTERIONS;

HYDROCARBONS;

REACTION KINETICS;

2 OXO 1H INDOL 3 YLIDENE; CHEMICAL COMPOUND; DIMETHYL ALLENEDICARBOXYLIC ACID; ISOQUINOLINE DERIVATIVE; METHYL 1 ALLYL 5 BROMO 1',1' DICYANO 4' (2 METHOXY 2 OXOETHYL) 2 OXO 1',11B' DIHYDROSPIRO[INDOLINE 3,2' PYRIDO[2,1 A]ISOQUINOLINE] 3' CARBOXYLIC ACID; METHYL 1 BENZYL 1',1' DICYANO 4' (2 METHOXY 2 OXOETHYL) 2 OXO 1',11B' DIHYDROSPIRO[INDOLINE 3,2' PYRIDO[2,1 A]ISOQUINOLINE] 3' CARBOXYLIC ACID; METHYL 1' (ETHOXYCARBONYL) 4' (2 METHOXY 2 OXOETHYL) 1 METHYL 2 OXO 1',11B' DIHYDROSPIRO[INDOLINE 3,2' PYRIDO[2,1 A]ISOQUINOLINE] 3' CARBOXYLIC ACID; METHYL 1',1' DICYANO 4' (2 METHOXY 2 OXOETHYL) 1 METHYL 2 OXO 1',11B' DIHYDROSPIRO[INDOLINE 3,2' PYRIDO[2,1 A]ISOQUINOLINE] 3' CARBOXYLIC ACID; METHYL 1',1' DICYANO 4' (2 METHOXY 2 OXOETHYL) 2 OXO 1 (PROP 2 YNYL) 1',11B' DIHYDROSPIRO[INDOLINE 3,2' PYRIDO[2,1 A]ISOQUINOLINE] 3' CARBOXYLIC ACID; METHYL 1',1' DICYANO 4' (2 METHOXY 2 OXOETHYL) 5 METHYL 2 OXO 1 (PROP 2 YNYL) 1',11B' DIHYDROSPIRO[INDOLINE 3,2' PYRIDO[2,1 A]ISOQUINOLINE] 3' CARBOXYLIC ACID; METHYL 4',4' DICYANO 1' (2 METHOXY 2 OXOETHYL) 2 OXO 4',4A' DIHYDROSPIRO[INDOLINE 3,3' PYRIDO[1,2 A]BENZOTHIAZOLE] 2' CARBOXYLIC ACID; METHYL 4',4' DICYANO 1' (2 METHOXY 2 OXOETHYLIDENE) 2 OXO 1 (PROP 2 YNYL) 1',2',4',4A' TETRAHYDROSPIRO[INDOLINE 3,3' PYRIDO[2,1 A]QUONOLINE] 2' CARBOXYLIC ACID; METHYL 4',4' DICYANO 1' (2 METHOXY 2 OXOETHYLIDENE) 5 METHYL 2 OXO 1 (PROP 2 YNYL) 1',2',4',4A' TETRAHYDROSPIRO[INDOLINE 3,3' PYRIDO[2,1 A]QUONOLINE] 2' CARBOXYLIC ACID; METHYL 5 BROMO 1' (ETHOXYCARBONYL) 4' (2 METHOXY 2 OXOETHYL) 1 METHYL 2 OXO 1',11B' DIHYDROSPIRO[INDOLINE 3,2' PYRIDO[2,1 A]ISOQUINOLINE] 3' CARBOXYLIC ACID; METHYL 5 BROMO 1',1' DICYANO 4' (2 METHOXY 2 OXOETHYL) 2 OXO 1 (PROP 2 YNYL) 1',11B' DIHYDROSPIRO[INDOLINE 3,2' PYRIDO[2,1 A]ISOQUINOLINE] 3' CARBOXYLIC ACID; METHYL 5 BROMO 1',1' DICYANO 4' (2 METHOXY 2 OXOETHYL) 2 OXO 1',11B' DIHYDROSPIRO[INDOLINE 3,2' QUINOZOLINE] 3' CARBOXYLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; FACILE MULTICOMPONENT REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 84856232266     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1289666     Document Type: Article

References (21)

1. Diels O, Alder K, Liebigs Ann. Chem. 1932 498 16
2. Acheson R M., Gagan J M. F., Taylor G A., J. Chem. Soc. 1963 1903
3. Acheson R M., Woollard J, J. Chem. Soc., Perkin Trans. 1 1975 438
4. Huisgen R, Morikawa M, Herbig K, Brunn E, Chem. Ber. 1967 100 1094
5. Huisgen R, Z. Chem. 1968 8 290
6. Crabtree A, Johnson A W., Tebby J C., J. Chem. Soc. 1961 3497
7. Nair V, Rajesh C, Vinod A U., Bindu S, Sreekanth A R., Mathen J S., Balagopal L, Acc. Chem. Res. 2003 36 899
8. Nair V, Remadevi B, Varma L, Tetrahedron Lett. 2005 46 5333
9. Butler M S., J. Nat. Prod. 2004 67 2141
10. Padwa A, Prog. Heterocycl. Chem. 1994 6 36
11. For a review, see:, Nair V, Menon R S., Sreekanth A R., Abhilash N, Biju A T., Acc. Chem. Res. 2006 39 520
12. Nair V, Sreekanth A R., Abhilash N, Bhadbhade M, Gonnade R C., Org. Lett. 2002 4 3575
13. Nair V, Devi R B., Pillai A N., Paul R R., Heterocycles 2007 73 249
14. Nair V, Devipriya S, Suresh E, Synthesis 2008 1065
15. Alizadeh A, Rostmania S, Synthesis 2010 1543
16. Reddy B V. S., Somasekhar D, Yadav J S., Sridhar B, Synthesis 2010 2069
17. Dömling A, Huang Y, Synthesis 2010 2859
18. Krause N, Hashmi A S. K., In Modern Allene Chemistry Vols. 1-2 Wiley-VCH Weinheim 2004
19. Ma S, Chem. Rev. 2005 105 2829
20. Lu X, Zhang C, Xu Z, Acc. Chem. Res. 2001 34 535
21. Nair V, Babu B P., Varghese V, Sinu C R., Paul R R., Anabha E R., Tetrahedron Lett. 2009 50 3716