Synthesis of benzothiadiazines, benzothiadiazepines, and benzothiadiazocines from intramolecular azide reactions and iodocyclisations

Nilesh Patel, Christopher S. Chambers, Karl Hemming

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

N-Homoallyl-substituted (2-aminoaryl)sulfonamides undergo intramolecular iodocyclisation to furnish aziridine-fused 1,2,6-benzothiadiazocines. The identical aziridine-fused 1,2,6-benzothiadiazocines were also available from an intramolecular azide to alkene 1,3-diploar cycloaddition involving the corresponding N-homoallylic (2-azidoaryl)sulfonamides in boiling carbon tetrachloride. The use of boiling DMF as solvent for the same reaction gave pyrrolo-fused benzothiadiazines. Intramolecular azide-alkene cycloadditions also allowed access to aziridine-fused pyrrolobenzothiadiazepines and pyrrolobenzodiazepines.

LanguageEnglish
Pages3043-3047
Number of pages5
JournalSynlett
Issue number18
Early online date9 Oct 2009
DOIs
Publication statusPublished - 21 Dec 2009

Fingerprint

Benzothiadiazines
Azides
Cycloaddition
Sulfonamides
Alkenes
Boiling liquids
Carbon Tetrachloride
aziridine

Cite this

@article{eb426b2bf3814587b679ba686aa69a58,
title = "Synthesis of benzothiadiazines, benzothiadiazepines, and benzothiadiazocines from intramolecular azide reactions and iodocyclisations",
abstract = "N-Homoallyl-substituted (2-aminoaryl)sulfonamides undergo intramolecular iodocyclisation to furnish aziridine-fused 1,2,6-benzothiadiazocines. The identical aziridine-fused 1,2,6-benzothiadiazocines were also available from an intramolecular azide to alkene 1,3-diploar cycloaddition involving the corresponding N-homoallylic (2-azidoaryl)sulfonamides in boiling carbon tetrachloride. The use of boiling DMF as solvent for the same reaction gave pyrrolo-fused benzothiadiazines. Intramolecular azide-alkene cycloadditions also allowed access to aziridine-fused pyrrolobenzothiadiazepines and pyrrolobenzodiazepines.",
keywords = "Azide, Aziridine, Benzodiazepine, Benzodiazocine",
author = "Nilesh Patel and Chambers, {Christopher S.} and Karl Hemming",
year = "2009",
month = "12",
day = "21",
doi = "10.1055/s-0029-1218278",
language = "English",
pages = "3043--3047",
journal = "Synlett",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",
number = "18",

}

Synthesis of benzothiadiazines, benzothiadiazepines, and benzothiadiazocines from intramolecular azide reactions and iodocyclisations. / Patel, Nilesh; Chambers, Christopher S.; Hemming, Karl.

In: Synlett, No. 18, 21.12.2009, p. 3043-3047.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of benzothiadiazines, benzothiadiazepines, and benzothiadiazocines from intramolecular azide reactions and iodocyclisations

AU - Patel, Nilesh

AU - Chambers, Christopher S.

AU - Hemming, Karl

PY - 2009/12/21

Y1 - 2009/12/21

N2 - N-Homoallyl-substituted (2-aminoaryl)sulfonamides undergo intramolecular iodocyclisation to furnish aziridine-fused 1,2,6-benzothiadiazocines. The identical aziridine-fused 1,2,6-benzothiadiazocines were also available from an intramolecular azide to alkene 1,3-diploar cycloaddition involving the corresponding N-homoallylic (2-azidoaryl)sulfonamides in boiling carbon tetrachloride. The use of boiling DMF as solvent for the same reaction gave pyrrolo-fused benzothiadiazines. Intramolecular azide-alkene cycloadditions also allowed access to aziridine-fused pyrrolobenzothiadiazepines and pyrrolobenzodiazepines.

AB - N-Homoallyl-substituted (2-aminoaryl)sulfonamides undergo intramolecular iodocyclisation to furnish aziridine-fused 1,2,6-benzothiadiazocines. The identical aziridine-fused 1,2,6-benzothiadiazocines were also available from an intramolecular azide to alkene 1,3-diploar cycloaddition involving the corresponding N-homoallylic (2-azidoaryl)sulfonamides in boiling carbon tetrachloride. The use of boiling DMF as solvent for the same reaction gave pyrrolo-fused benzothiadiazines. Intramolecular azide-alkene cycloadditions also allowed access to aziridine-fused pyrrolobenzothiadiazepines and pyrrolobenzodiazepines.

KW - Azide

KW - Aziridine

KW - Benzodiazepine

KW - Benzodiazocine

UR - http://www.scopus.com/inward/record.url?scp=72049133428&partnerID=8YFLogxK

U2 - 10.1055/s-0029-1218278

DO - 10.1055/s-0029-1218278

M3 - Article

SP - 3043

EP - 3047

JO - Synlett

T2 - Synlett

JF - Synlett

SN - 0936-5214

IS - 18

ER -