Micelles catalyzed one pot regio- and chemoselective synthesis of benzo[a]phenazines and naphtho[2,3-d]imidazoles “in H2O”

• • • Tetrahedron Letters, In Press, Accepted Manuscript, Available online 28 September 2014
• Vishnu K. Tandon, 
• Manoj K. Verma, 
• Hardesh K. Maurya, 
• Sandeep Kumar

• • Received 23 July 2014, Revised 20 September 2014, Accepted 22 September 2014, Available online 28 September 2014

    DOI: 10.1016/j.tetlet.2014.09.103

    
    

    Abstract

    An efficient, novel and concise one pot regio- and chemoselective synthesis of benzo[a]phenazines (4) and naphtho[2,3-d]imidazoles (8) has been accomplished in excellent yields by nucleophilic substitution reaction of 2,3-dichloro-1,4-naphthoquinone (1) with o-phenylenediamine (2) and benzamidines (7) respectively “in H₂O” using base and micelles (SDS) as catalyst. Analogues reaction of 2,3-dichloro-1,4-naphthoquinone (1) with 2-aminobenzenethiol (9) under identical conditions led to formation of a mixture of benzo[b]phenothiazine (10), benzo[a]phenothiazine (11) and benzo[a]-1,4-benzothiazino-3,2-phenothiazine (12) in 17, 23 and 57% yields respectively.