Chemistry of Substituted Thiazinanes and Their Derivatives.

Alaa A Hassan,Stefan Bräse,Ashraf A Aly,Hendawy N Tawfeek

doi:10.3390/molecules25235610

Alaa A Hassan, Stefan Bräse + Show 2 more

Open Access

https://doi.org/10.3390/molecules25235610

Copy DOI

Abstract

Thiazinanes and its isomeric forms represent one of the most important heterocyclic compounds, and their derivatives represented a highly potent drug in disease treatment such as, 1,1-dioxido-1,2-thiazinan-1,6-naphthyridine, which has been shown to have anti-HIV activity by a mechanism that should work as anti-AIDS treatment, while (Z)-methyl 3-(naphthalen-1-ylimino)- 2-thia-4-azaspiro[5 5]undecane-4-carbodithioate showed analgesic activity, cephradine was used as antibiotic and chlormezanone was utilized as anticoagulants. All publications were interested in the chemistry of thiazine (partially or fully unsaturated heterocyclic six-membered ring containing nitrogen and sulfur), but no one was dealing with thiazinane itself which encouraged us to shed new light on these interesting heterocycles. This review was focused on the synthetic approaches of thiazinane derivatives and their chemical reactivity.

Highlights

IntNroitdruocgteino–nsulfur containing heterocycles represent a widespread group of heterocyclic compNoiutrnodgse.nT–hsuelsfeutrycpoenstaoifnihnegtehreotceyroclceysclceosnrsetprurecstendtaa lwaridgesnpuremadbegrrouf pdroufghsetuesreodcyicnlitchceotmrepaotumnednst
The 1,2-hydride migration product 44 could not be detected in reactions catalyzed by p-TsOH. In the latter case, the Z-α-phenyl-β-enamino ester 43a was formed as the major product (43a/43b = 95:5)
Product 44 could not be detected in reactions catalyzed by p-TsOH

Summary

Chemistry of Substituted Thiazinanes and Their

CDheerimvaistitvryesof Substituted Thiazinanes and Their Derivatives Alaa A. Hassan 1,*, Stefan Bräse 2,3,*, Ashraf A. Received: 25 July 2020; Accepted: 18 August 2020; Published: 24 August 2020 Academic Editor: György Keglevich. RAebcesitvraedct::25ThJuialyz2in0a20n;eAscacenpdteidt:s1i8soAmugeursict 2f0o2r0m; Psurbelipshreesde: n2t8 Nonoeveomfbtehre20m20ost important heterocyclic. Acobmstpraocutn: dTsh, iaanzdintahneeirs daenrdiviattsiviseosmreeprricesfeonrtmeds arehpirgehselyntpotneentofdrtuhge minodsitseimaspeotrrteaantmt heenttesroucyhcalisc, c1o,1m-dpiouxinddos-,1a,2n-dthitahzeiinradne-r1i,v6a-ntiavpehstrheyprriedsinene,tewdhaichhighhalsybpeoentensht odwrungtoinhdaivseeaasnetit-rHeaIVtmaecntitvsiutychbyasa, 1m,1e-cdhiaonxidsmo-1th,2a-thsihaozuinldanw-1o,6rk-naaspahnthtiy-AridIDinSet,rweahtimchenhta,swbheielne (sZh)o-wmnetthoyhl a3v-(enanpthi-thHaIlVena-c1t-iyvliitmy ibnyo)am2-ethcihaa-4n-iasmzastphiartos[5ho5u]uldndweocarknea-s4-acnatrib-AodIDithSiotraetaetmsheonwt,ewd hanilael(gZe)s-imc aectthiyvlit3y-,(cneapphhrtahdailneen-w1a-ysluimseidnoa)s2a-ntthiibai-o4t-iaczaanspdircoh[l5or5m]uenzdaencoannee-w4-acsarubtoildizitehdioaasteasnhtiocwoaegdualannatlsg.eAsicllapcutibvliitcya, tcieopnhsrwadeirneeiwntaesreussted ains athneticbhioetmicisatnryd ocfhtlhoriamzienzean(poanretiwallays ourtifluizlleyduanssantutircaoteadguhleatnetrso.cAycllicpusibxl-imcaetmiobnesrwedereinigntceornetsateindining tnhietrcohgemn iasntrdy soufltfhuira)z, ibnuet(npoarotinaellywoarsfduellayliunngswatiuthrathediahzientaernoecyitcsleilcf swixh-michemenbceoreudrarginegd cuosntoainshinegd nietwrogliegnhtaonndtshuelsfeuirn),tebruetstninogohneetewroacsydceleasl.inTghiws ritehvitehwiazwinasanfoeciutseldf ownhtihche seynnctohuertaicgaepdpursoatochsehseodf ntheiwazliingahnteondetrhievsaetiivnetseraensdtinthgehiretcehreomcyiclaelsr.eTahctisivrietyv.iew was focused on the synthetic approaches of thiazinane derivatives and their chemical reactivity.

Introduction

HHNN SS

Findings

NR NR