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

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;

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

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Referenzen

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