One-Pot Microwave-Assisted Selective
Azido Reduction/Tandem Cyclization in Condensed and Solid
Phase with Nickel Boride

Nagula Shankaraiah; Nagula Markandeya; Marlene Espinoza-Moraga; Claudia Arancibia; Ahmed Kamal; Leonardo Silva Santos

doi:10.1055/s-0029-1216831

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Synthesis 2009(13): 2163-2170
DOI: 10.1055/s-0029-1216831

PAPER

One-Pot Microwave-Assisted Selective Azido Reduction/Tandem Cyclization in Condensed and Solid Phase with Nickel Boride

Nagula Shankaraiah^a, Nagula Markandeya^b, Marlene Espinoza-Moraga^a, Claudia Arancibia^a, Ahmed Kamal*^b, Leonardo Silva Santos*^a
^a Laboratory of Asymmetric Synthesis, Chemistry Institute of Natural Resources, University of Talca, P.O. Box 747, Talca, Chile
e-Mail: lssantos@utalca.cl;
^b Chemical Biology Laboratory, Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27193189; e-Mail: ahmedkamal@iict.res.in;

Weitere Informationen

Publikationsverlauf

Received 26 January 2009
Publikationsdatum:
19. Mai 2009 (online)

Abstract
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Abstract

An efficient and inexpensive method using microwave-assisted irradiation with Ni₂B for the syntheses of aromatic amines, pyrrolobenzodiazepines as well as pyrroloquinazolinones was developed. This protocol was applied in the tandem resin-cleavage, azido reduction, and cyclization of compounds 3 and 5 that afforded substituted pyrrolo[2,1-c][1,4]benzodiazepines 4 and 6 in a one-pot manner. The microwave-assisted irradiation reactions enhanced yields with very short reaction times in contrast to the conventional thermal reactions.

Key words

pyrrolo[2,1-c][1,4]benzodiazepines - pyrroloquinazolinones - azido reductive cyclization - nickel boride - microwave irradiation

References

1a Scriven EFV. Turnbull R. Chem. Rev. 1988, 88: 297

Suche in Google Scholar
1b Brase S. Gil C. Knepper K. Zimmermann V. Angew. Chem. Int. Ed. 2005, 44: 5188

Suche in Google Scholar
1c Azides and Nitrenes: Reactivity and Utility Scriven EFV. Academic Press; New York: 1984.
1d The Chemistry of the Azido Group Patai S. Wiley; Chichester: 1971.
2a Tiecco M. Testaferri L. Santi C. Tomassini C. Marini F. Bagnoli L. Temperini A. Angew. Chem. Int. Ed. 2003, 42: 3131

Suche in Google Scholar
2b Sridhar PR. Prabhu KR. Chandrasekaran S. J. Org. Chem. 2003, 68: 5261

Suche in Google Scholar
2c Hays DS. Fu GC. J. Org. Chem. 1998, 63: 2796

Suche in Google Scholar
2d Goulaonic-Dubois C. Hesse M. Tetrahedron Lett. 1995, 36: 7427

Suche in Google Scholar
2e Samano MC. Robius MJ. Tetrahedron Lett. 1991, 32: 6293

Suche in Google Scholar
2f Rolla F. J. Org. Chem. 1982, 47: 4327

Suche in Google Scholar
2g Kondo T. Nakai H. Goto T. Tetrahedron 1973, 29: 1801

Suche in Google Scholar
2h Corey EJ. Nicolaou KC. Balanson RD. Machide Y. Synthesis 1975, 590
3a Rao HSP. Siva P. Synth. Commun. 1994, 24: 549

Suche in Google Scholar
3b Alverez SG. Fisher GB. Singavam B. Tetrahedron Lett. 1995, 36: 2567

Suche in Google Scholar
4 Molina P. Diaz I. Tarraga A. Tetrahedron 1995, 51: 5617

Crossref Suche in Google Scholar
5 Ramesha AR. Bhat S. Chandrasekaran S. J. Org. Chem. 1995, 60: 7682

Crossref Suche in Google Scholar
6a Capperucci A. Degl’Innocenti A. Fumicello M. Mauriello G. Scafato P. Spagnolo P. J. Org. Chem. 1995, 60: 2254

Suche in Google Scholar
6b Kamal A. Reddy BSP. Reddy BSN. Tetrahedron Lett. 1996, 37: 6803

Suche in Google Scholar
7 Huang Y. Zhang Y. Wang Y. Tetrahedron Lett. 1997, 38: 1065

Crossref Suche in Google Scholar
8a Benati L. Bencivenni G. Leardini R. Minozzi M. Nanni D. Scialpi R. Spagnolo P. Zanardi G. J. Org. Chem. 2006, 71: 434

Suche in Google Scholar
8b Benati L. Bencivenni G. Leardini R. Minozzi M. Nanni D. Scialpi R. Spagnolo P. Zanardi G. J. Org. Chem. 2006, 71: 5822 ; and references cited therein

Suche in Google Scholar
9a Pogorelica I. Filipan-Litvica M. Merkasa S. Ljubica G. Cepaneca I. Litvic M. J. Mol. Catal. A: Chem. 2007, 274: 202

Suche in Google Scholar
9b Molvinger K. Lopez M. Court J. Tetrahedron Lett. 1999, 40: 8375

Suche in Google Scholar
9c Molvinger K. Lopez M. Court J. J. Mol. Catal. A: Chem. 1999, 150: 267

Suche in Google Scholar
9d Santos LS. Pilli RA. Synthesis 2002, 87
9e Khurana JM. Kukreja G. Synth. Commun. 2002, 32: 1265

Suche in Google Scholar
9f Osby JO. Ganem B. Tetrahedron Lett. 1985, 26: 6413

Suche in Google Scholar
9g Nose A. Kudo T. Chem. Pharm. Bull. 1989, 37: 816

Suche in Google Scholar
10a Kamal A. Ramana KV. Rao MV. J. Org. Chem. 2001, 66: 997

Suche in Google Scholar
10b Kamal A. Damayanthi Y. Reddy BSN. Lakshminarayana B. Reddy BSP. Chem. Commun. 1997, 1015
10c Kamal A. Shankaraiah N. Markandeya N. Reddy KL. Reddy ChS. Tetrahedron Lett. 2008, 49: 1465

Suche in Google Scholar
10d Kamal A. Reddy GSK. Reddy KL. Tetrahedron Lett. 2001, 42: 6969

Suche in Google Scholar
10e Kamal A. Reddy GSK. Reddy KL. Raghavan S. Tetrahedron Lett. 2002, 43: 2103

Suche in Google Scholar
11 Trost BM. Angew. Chem., Int. Ed. Engl. 1995, 34: 259 ; and references cited therein

Crossref Suche in Google Scholar
12a Kappe CO. Angew. Chem. Int. Ed. 2004, 43: 6250

Suche in Google Scholar
12b Lidstrom P. Tierney J. Wathey B. Westman J. Tetrahedron 2001, 57: 9225

Suche in Google Scholar
13 Bartoli G. Antonio GD. Giovannini R. G iuli S. Lanari S. Paoletti M. Marcantoni E. J. Org. Chem. 2008, 73: 1919

Crossref Suche in Google Scholar
14 Thurston DE. In Molecular Aspects of Anticancer Drug DNA Interactions Neidle D. Waring MJ. Macmillan; London: 1993. p.54-88
15a Kaneko T. Wong H. Doyle TW. J. Antibiotics 1984, 37: 300

Suche in Google Scholar
15b Jones GB. Davey CL. Jenkins TC. Kamal A. Kneale G. Neidle S. Webster GD. Thurston DE. Anticancer Drug Des. 1990, 5: 249

Suche in Google Scholar
15c Kaneko T. Wong H. Doyle TW. Tetrahedron Lett. 1983, 24: 5165

Suche in Google Scholar
16 Kamal A. Howard PW. Reddy BSN. Reddy BSP. Thurston DE. Tetrahedron 1997, 53: 3223

Crossref Suche in Google Scholar
17a Thurston DE. Bose DS. Chem. Rev. 1994, 94: 433

Suche in Google Scholar
17b Kamal A. Rao MV. Reddy BSN. Chem. Heterocycl. Comp. 1998, 1588
17c Kamal A. Rao NV. Chem. Commun. 1996, 385
18 Blackburn BK. Lee A. Baier M. Kohl B. Olivero AG. Matamoros R. Robarge KD. McDowell RS. J. Med. Chem. 1997, 40: 717

Crossref Suche in Google Scholar
19 Wright WB. Brabander HJ. Greenblatt EN. Day IP. Hardy RA. J. Med. Chem. 1978, 21: 1087

Crossref Suche in Google Scholar
20 Di Martino G. Massa S. Corelli F. Pantaleoni G. Fanini D. Palumbo G. Eur. J. Med. Chem. 1983, 18: 347

Suche in Google Scholar
21 Karp GM. Manfredi MC. Guaciaro MA. Ortlip CL. Marc P. Szamosi IT. J. Agric. Food Chem. 1997, 45: 493

Crossref Suche in Google Scholar
22 Antonow D. Jenkins TC. Howarda PW. Thurston DE. Bioorg. Med. Chem. 2007, 15: 3041

Crossref Suche in Google Scholar
23a Schlessinger HI. Brown HC. Finholt AE. Gilbreath JE. Hoestra HR. Hyde EK. J. Am. Chem. Soc. 1953, 75: 215

Suche in Google Scholar
23b Brown CA. J. Org. Chem. 1970, 35: 1900

Suche in Google Scholar
23c Hoffer LJE. Schultz J. Panson RD. Anderson RB. Inorg. Chem. 1964, 3: 1783

Suche in Google Scholar
23d Seltzman HH. Berrang B. Tetrahedron Lett. 1993, 34: 3083

Suche in Google Scholar
24 Kamal A. Ramana KV. Ankati HB. Ramana AV. Tetrahedron Lett. 2002, 43: 6861

Crossref Suche in Google Scholar
25 Amin AH. Mehta DR. Nature 1959, 183: 1317

Crossref Suche in Google Scholar
26 Al-Shamma A. Drake S. Flynn DL. Mitscher LA. Park YH. Rao GSR. Simpson A. Swape JK. Veysoglu T. Wu STS. J. Nat. Prod. 1981, 44: 745

Crossref Suche in Google Scholar
27 Grange JM. Snell NJ. J. Ethnopharmacol. 1996, 49: 5091

Suche in Google Scholar
28 Kamal A. Reddy KL. Devaiah V. Shankaraiah N. Reddy GSK. Raghavan S. J. Comb. Chem. 2007, 9: 29

Crossref Suche in Google Scholar
29 Kamal A. Reddy KL. Devaiah V. Reddy GSK. Tetrahedron Lett. 2003, 44: 4741

Crossref Suche in Google Scholar
30a Gronnow MJ. White RJ. Clark JH. Macquarrie DJ. Org. Process Res. Dev. 2005, 9: 516

Suche in Google Scholar
30b Ondruschka B. Bonrath W. Stuerga D. In Microwaves in Organic Synthesis 2nd ed.: Loupy A. Wiley-VCH; Weinheim: 2006. Chap. 2. p.62

Suche in Google Scholar
31 Kavala V. Naik S. Patel BK. J. Org. Chem. 2005, 70: 4267

Crossref Suche in Google Scholar