Studies on chalcogen-containing heterocycles. Part 38: Regio- and stereoselective tandem addition-iodocyclization of 2-ethynylphenyl isothiocyanates with N- and O-nucleophiles affording 4-(iodoalkylidene)benzo[d][1,3]thiazines

被引：23

作者：

Sashida, Haruki ^{[1
]}

Kaname, Mamoru ^{[1
]}

Minoura, Mao ^{[2
]}

机构：

[1] Hokuriku Univ, Fac Pharmaceut Sci, Kanazawa, Ishikawa 9201181, Japan

[2] Kitasato Univ, Sch Sci, Dept Chem, Minami Ku, Sagamihara, Kanagawa 2520373, Japan

来源：

TETRAHEDRON | 2013年 / 69卷 / 31期

关键词：

1,3-Benzothiazine; Isothiocyanate; Tandem addition-cyclization; Iodocyclization; 6-exo-dig Mode; ELECTROPHILIC CYCLIZATION; INTRAMOLECULAR CYCLIZATION; 1-BENZOTELLUROPYRYLIUM SALTS; TERMINAL ALKYNES; SYNTHETIC METHOD; ALPHA-PYRONES; DERIVATIVES; IODINE; ISOCOUMARINS; EFFICIENT;

D O I：

10.1016/j.tet.2013.05.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The treatment of the o-ethynylphenyl isothiocyanates with primary and secondary amines in 1,2-DCE, followed by the addition of 12 and then heating resulted in the regio- and stereoselective tandem addition-iodocyclization to give the (4E)-2-amino-4-(1-iodomethylidene)benzo[d][1,3]thiazine derivatives as the sole product in high yields via the 6-exo-dig mode cyclization. The 2-alkoxy-1,3-benzothiazines were similarly produced from the o-ethynylphenyl isothiocyanates and the corresponding sodium alkoxides. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：6478 / 6487

页数：10