Synthesis of naphtho[2',3':4,5]imidazo[2,1-b][1,3]-thiazole-5,10-dione and naphtho[2',3':4,5]imidazo-[2,1-b][1,3]benzothiazole-7,12-dione

The reaction of 2,3-dibromo-1,4-naphthoquinone with 2-aminothiazole in MeONa/MeOH at 60oC for 3 h gave naphtho[2',3':4,5]imidazo[2,1-b][1,3]thiazole-5,10-dione in 64% yield. The reaction of 2,3-dibromo-1,4-naphthoquinone with 2-aminobenzothiazole under the above-mentioned conditions gave 2...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2010-09, Vol.46 (5), p.613-616
Main Authors: Khalafy, J, Ghezelbash, Z. D, Mahmoody, M
Format: Article
Language:English
Subjects:
2,3-dibromo-1,4-naphthoquinone
Chemistry
Chemistry and Materials Science
naphtho[2',3':4,5]imidazo[2,1-b][1,3]benzothiazole-7,12-dione
naphtho[2',3':4,5]imidazo[2,1-b][1,3]thiazole-5,10-dione
Nitriles
Organic Chemistry
Pharmacy
ring cyclization
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The reaction of 2,3-dibromo-1,4-naphthoquinone with 2-aminothiazole in MeONa/MeOH at 60oC for 3 h gave naphtho[2',3':4,5]imidazo[2,1-b][1,3]thiazole-5,10-dione in 64% yield. The reaction of 2,3-dibromo-1,4-naphthoquinone with 2-aminobenzothiazole under the above-mentioned conditions gave 2-(benzo[d]thiazol-2-ylamino)-3-bromonaphthalene-1,4-dione in 64% yield, which on treatment with Na/THF or NaN₃/acetone under reflux conditions gave naphtho[2',3':4,5]imidazo[2,1-b][1,3]- benzothiazole-7,12-dione in 69 and 56% yields, respectively.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-010-0554-6