Advances in Heterocyclic Chemistry

178 Pages·1969·10.53 MB·English

by  A. R. Katritzky, A. J. Boulton (Eds.)

Edbtosial Advisory oord

A Alber,
AoW, Baboon
G, olor

8, Geenowite

J Gu

R. Hubsgen

N. K. Rushet’or
JH Rd

Advances in

HETEROCYCLIC
CHEMISTRY

Bilited by
AR. KATRITZKY
A. J. BOULTON,

(@) Volume 10

Academic Prew + New Yor sudtendia +

1969
Contributors

A, van sy Fate unis Phycce, Dok, owas)

J. Ritean, Maperimontn) lowing, Bowdiga Feat nt Pde diy
Boog, Fitri. ir 199:

1D. Se U. Braon. Famine nf Chenisty, Monash Uniwrsine
gen, Prt, Ate 10)

1b, Pots news = Deparmnee of Chery, okie 9 Gora Arai,
te duds Honnel Paiscrty, Cowbro, dC. stots

Baucus, Malt of encent ioe, ate

Noe, Hort, Pani)

sec Diab Acton i: sane on Botan, dase

fo spl, Lavin, Rest Carey (2

FS ems Oroteant of Medical Chaney, The dvstaline
‘ational Canes, Cuabree, AO. febB

B.A Tiescnce, dant Mepaaat Laboatery, asians Rew
Conouit i Coan Hatfer, Nara Seti, Ct 6

Waal bons, Depormne of Pvermcey, vires Aion in Biron
am, Bicninnne Baa! 1431

S Katrin? Amie Fosional fobwaey, atonal Aasorek
Coanal ef Coaada, Leifer, Hera Seo, Condit

ALE. Mamed Dopasensnt9f Csr. Marcond Cnisrsity, mn
Tell Hroabnaete i118)

1B sowstrin, Laas of Uiade Chest, Matin taller Taien
si, Pe Waterers aang 13

Tu re Depwrtmontey henry Moreen! Uxoewy. Ceres,
“Saozncat 113

S. Wirmracus, Tapani of Furnacy, Maronaty of ton Db

Wong, Hiresegtan, Becht (148)

4

st che
Preface

“Tees elem nf hc al abi ain shat
rat af which del ait the geveral cheery a spe gros
Invenyels compeuide, paiepyiitines |W fori aed DC
‘Wihhite) eveanaas x78. F Boston and PD. CBeeh) iinet
9 hate was Ey Sse prylaen salle (ALT. Balsa,
§W. deeth, and Winer. The ecaining ote are minroed
ii file Geipnand erent eA Uatuth and 8, Kresge aod
Ait eye he dvd ate od, Bop, DU. Dake aed Te
Ilromtthvoorsalwnat fs Ube pice fe presen
eatibatecs rome Pore se esate howe est

‘Wr nk Cae sally aud cables er Wee sopoention =i
non lea plats Eesha 008 eR,

ecm Baghoud AK Katerreny
Bronk, 08 os Renin
Concents

Venoofirvers

i Rate hg &
Fla Tok Grignanl Regents
Baron of doe Scan Mees i

eines
Pyrsopyeiiine

Preys eit rn gt! tee

yeh Hpdevsame acs

Hprylon site
fort, Syrthee

Bowetiraxans

Pevwertf Mat ttm Ste Anoncin

& ‘Segeer Aart esac pet
2 at. bnung as 2, SH rie

1 baeoneton

‘The benetunaan Uovzofusan oxide, Sa-buaso-1 20a
Ainalet-orkin, we 15 bemoan aside 1] rug e3cte i
"ew revived bly cs eevee eovrionn, acta by Rakion Hd
Praus Boyes,” en lr? Ew nal veut dawu* voveet the
lteratine bed TSAR, tal aloe chal date there ans bon
tse the 202 Thi, ee. jes Ue etl bg cov
ge mom, aud ia acpaesties fen He auinenaie 12x
(idee Un Tusuacte, i consider 9 les Tersmno fed me
poonesin ts sacle, abo othe Hat Faso eet
Teste tron concent amd ican,

a ak
ror oe

‘Var Uemraundlated desivabive aapblie L2efarosan i ners
led ascot Un ptr (2 sav. Im the ere the em

2 mpnkforas may fees he fnew these ae Haaser as
fox a ,2edinattinted naphclene. thong fie thd fo
poskapa litle lace lo ow, ve wry gauninati aoe
Eten tin This shay

1. Atrenore

‘Tae erste oa Hengofimosan is contre ly mdb by
suuihireon omtetaing Lei eeuclury nich ee mvt a
itn “Faas, Rebtee Bap’ sloder eben it Yelaoe 7 fas
Aasicato of opsvoney, aepioed a2 einai, aol nto ae

me tact np 8 ae

9 inugen remmpamada; ive Fie Baron Hh exe Volare
Site diemdinstines, aad i te Beoend Suyyinnt aw tn
‘Paine leben a anadincle ode

Guest sabia serewers al Hlllory aa Wed and, fre
atlioritvovar, Haunnici 9! ve vurevursal Ue bisory 6
Gieeuye poblen falely Ii, an sor Hanno de auy wae Oe
eased proponig's olatne from ths of themicreezlierivncne, vm
ual ren cy Brie inn tn The niet farms f0 be
Sngpottes cond 4 i entoeston wilh 12 ra shiduanozan, die
esr Ry Kote fon Thos i 88, wee open Ich oie
(uw ist tne fsa yetonide ete et, lave icbonzatieenars

an
CAs Ol Cle
cee Or»
f

re nuke wee onidicing apis wai dy nor show olor prupartian
tertenniy ne alg wh the rmoey liege ad aseecont ora
itoce youps obhowgh Hon urna been! und cylal propaga oF
‘Caaheves caus er Taking The feosen arastre 8), which
Iie ern Sie (Li tot tela sae sappeced br sen ead
Hoe 1613, ht lurid «Foor len bso i becsnse tar
tastrnmedsivad seretare of B sequel Heat € eral Goubstnbd
fuarjaurds should Torn to iaowaie ais. Hosmer, hepoeaeaite
CSidition {a genera ino o far ubiaadag benvationrens fom

ep ane on tiie (aly nn
eer ree FR. Sota, 7 i.e
4 sc ROMEEER ADH to [oe TL

oionitines, eee Section IF) of Beainoceritrwslnoue and
qehoe eritua}imve Id to sip ese reethybvonoturowt Ur
fatdbprnsivadtanrvany, Patel ord Honkee!=abteine te aur
ranoneowchnnratinosna Hen ten tomers omntrophw FLUC
Tee Sedan rete locale bor ad erg oP eapbchs=

PE ge Oe ae SOIL

oes

eye ie OE,

[a eftoxan! "Ths bapenfansean ede steatane Br Da
rice hy Dnnuiek aie 1981 bs cera Uke evan
‘Cpevubcaon aid berzatcazns, and alos fron ysiachat te
see erred S uvet thn aruatute 8 abd 8, Tar ago sg
foeted not n ropid fvleeseneericn ul abahle ino able nae,
Seong ie the dtnen trucour 6. (Seoul be eee Fat

Eretdocation single conn Pion pace Corres wus 4 he
‘eyed.

pt » i
ry eoph g,
wy Ly

Te Ns tye a alleng th saben el nage
sean tooth race tne wh
weer nolan erp 9 an A) To rope romance
Thain etniag toe tawoe ptilebsbersere for Be pare
Sr, Ey ru boneny, and mr stn Man ge.

Sg teeter mente

fee LH unre seas

apse eee
beets 7 eee

sunt aboely forward ie wus deniymusa Ty: eeveral arvups oF
a Seer sete marty wig, 1 HAC en oF Doh ATR
Te cy nad Roray Ceakon TEL Liv dere, lo e itech
Ma lag cas of ha res ftnes cf Gi besa,
oe eer hy hoen tal af Slams,» nat beth sow
aa 8 off canted systrs 1 15) Aas 0 be
er eeu of ret tenuctirowars gh ur only one
Se ester ibere wae lak see Tanlaank.! Spat fon
Pee onthe theenadgrenis pasunaters jowsided by hactie
erate rege 6 wna toned, sod
a eee yiiiy ae 2eetnvwstitn re? Venartiaole 1 éxikes 2
Fee thet ede nota reece a i boc The
a ladtary catuonivazee Hover Mimaki
TES Tah eetow onlorof ot reatooe of berwirosin, «hich
toe ye cue uring tu suongy ergmnents MEMexy sul
Tabanan ae th er possibiies ane Par es koh. The
a eegiie ommlante Fr the MtexOouFeRon oom vat
Hee en ADE spent el eapers ure. 9 wil le
rea Serean Dit In oi oli page, only ons wien of
Ste te beomobevmafuraany we9eh Seton TDi
enamine lel b tighten she Seen
av capone fn Pig ren. Vian, Goes rd aactsTbewe,
Tinea van pe ene melee wis, Danse ei ten
Nwosnort anoe bs aolae” aeparvtely ar onal trugetaterm
‘Shrub thy mews ken oe tv ba 3ox the emia
re a ariel eugcosing hm omest vers, Tho
Ree Minicom or onsale, sil br dare hed we Sot
CEN uovias engulf Ee ewe sald she yal, aca 9
« ccecnammion snes memos (801 AL

ptoalar tautenee eo hednsipantod his el be deny dbbelcine
Fae stunral

Tinnetr ad Roxcoters tae dincevad he electric enorurs of
romebor ef mite aoe poten alteean 2p ease, naling Bom
‘roams. uiag the natin appa

1M, Syoetroscophe nd Oster Piel rapectiny

A, es ences Sema

Nampwanaticinvetigation at th ribratioctthe bavctiyosss,
swloratvits beeuseporied: Ineued dete we aval for e ataee
"fivnanas enantio 5a 168 Use ou ae Ee
Tenors oleae 1USE, 1500 1605, and 150 ne Tei ie
Fnac shim’ sapere Us enr alm ‘aance 9 eorece
tent of ot nowt sho reverse oor commen osc a he
eve of emitted beraorersans, sd a2 Sey weil lo linge
eulie pasjawm, Ose uae Dane ry De weer lie, Woes
fir Zikgoridefuonum facubanms Burson) only oben aE 12
‘ented in tien"

‘Patna can eed ae ogg yh, Piri
sed Kuutinar hy rape Hen with Uomo
Bf, who fod siniarkies with fexosaas"” and nstean sor
frond aa Ly athe 2= 0" "Hesatmalisemin” nas ane
EP'TR and Ravan spetoionnngy lr eck tthe Irvenefaroset
ovetare

SI fee Vong 19a MEA Messe
age anes

[en THB escorts :

rucvrores evete

Emtraicapodral onsbdnatene were inroied by Bogor at ig
fuser nf the feodiitrono-" teuolurs aid Tye Maley aud Wao!
gone u2 cushion elation forthe \ eciesesetans, Thc
peal afeotemileuteametuninscs dare boca veperted

I geortal, by low-cnegy bord pean appre, which Sn bows
urwasn Heel? viunglyveaping, a eobaieaiel mpoad,

eek seem ge eet wt a

for amply he rotor Ueistive, he aces become wane 0
lees mepovto hom a higarryuoncy fase wh ova find
snmustate aud lame requsbcy bed wich lve wel deta! serach

(Gur he ddagger, Thar aura very sina 2 tat shoe
® scempuarn ast nono Seo LC]

‘yumm, empbaniing ther snlaay ora anelilern th
groapscl coalpoude ae ig, ith the ororaly Weulrawdounting
‘dimetiunno subestacat, the ino: wing Barats wel i
re iain ie opel en

1 Nocaan Yaevenie Bratnsnon SR

he Seek iene fin a armsranuial ene fr the be
fvoran eleva ned I i laren, oa 38 we pO
IGL by gorse grow of arkansas eyotan Bec ADeS

spendnag At oe Invapmarie 149 5am were ATID:
spectre “oon, bien oteames proses cay mnie bere ita
veh fuapetice aul sul Lh gi bel fn
serene fn and abarain ene sng 4 welgelned
spereeteiot (4rd) spehrors above Joy Bu aaknace Joe th
Seireso woe dt Ine fe Taaorericn ui Hl hence ae

Be. mur cue

adh Mia alls fv 4 itacmobescotuneun and 5-metly
Beneteau Lave bert perm] ly Bgl? 77. oid
Rr ebthe RAE apocem of Lemdurvemng i 61831 Oder
Tagamande sive: pat ve ct qld HL va Lager
iMate dace Selon 2% wetloaye od a mine bo aad

Sie Benn, aseehglt nia eluant earl,
Phowtemita Ste aud 4ediehleen and Seibeoacber
Farueact 1°" Nieeawaatosen, 4 eke goal asauaple, of

YP wows spect far tho mo ditt pace teenth,
sean’ ark peel 9 Ra ttn opiee a9 eds oF
the Dacie ofthe sera rifle ofthe parsed Th wan Carey
Slow thst the Gaze sree prdeotnaes tote est of slant
$085 nthe naam Bal alto gure a hat teuperatare
Teo, 2,4 Rilsebecnsuraan shige tow Ie Foo ee
footw lenyarabnes oud ein ely stented
hits meieiedy ne the Fit ime ona erates. yo
holst ue spectee. Frid at efansean nay al: the
‘Phe eroetre 1p wituuly se 72, Fama (22 ah

ee ae
a re Y ee

ne ols Wc ld ava wie Usving’segution, rehitag
vigrenen rent testo Ua vation evergy AC, wheather
heave ined tas Ampherive pacurcigr # he Polls obtaiend are
(alls eins or a tes {eal 98 An all Me enbetel
eu Fete stern, a shut 14 here fsbo
‘tmouo caaapearan di veloc FL Skervoln w bese oye
buat thie appoare to Us ereueous- IA camoetion off, valuee woth
oe af aha: Heya 7 pos feo aged
‘A50 ence enoet tom tae Seletins peor eon

BN Act Balak ME ea and RE Fam
ry ad. wctTO awe sama (See MH

5, Raver Promina
Tengafasoans ia avers pl elle ertaling ido ae dng
poiot 1. Tea digele wonent eieen hy Unppl ay B20 D. and en
owes of egitofber bensolaaonaine wa wtler elas tiviis,
Fra molting pala, a soy seecaded Ite appeaslly sts
“ols bot fo bn 2 a is dross ane oy lemon
lng pins" toneSunvean tn Kev by Ruined Bea,
nko Pets X oe rte

“The phys prncertion awsoratd wits the pase, wc Ihe
Liquid ver svar one he eaity at Plows torrets
rvofineesit ard “smenhplbe wots ae oven hy mma
(Hat! Phe parunnr ae oee wee oeratieed ly Bier ot

1, Peopatacon of Bourefurwane

Reread sy Vache yada ivnmsliociie.
‘Diafinw teoauroxnn Hewento, Fl sri 9 0 es
4p Bex etind.** Beale onlduiug syoute Facile salve fo
sponte” © taomaie len Tories sad wien und Che
‘Retiedisn poslane velunalg wheats ogni aiesnoncine
To mitraupbese is feadly sails wil tare ree aot pees
‘he one, other route, sh osidetien of oaitrnine™ urt the
Shenson of ope an ny nor eam

‘i oxiation of »aitenailies bi banaue was disor
by Gees aaa Rowe lu one wine peri, Aho
lead har hoe tel etsy 2 rcogoualy Fan

ely penorerasiss as

ise the axseesal ete, moving af aqacour tl li
Ssimdocss with Eyllivkvauchne, {00 emamgle, the probe fe
Fellow tinechosy emma, rather Wan the 8 WIRD. ce
found” fare Seti VIL, Nu Benanfaoren as ebesined fom
Sitep pherglonedincias,?* Laps Amirali, oF
uate Sartopihene™ hy ais watbod. Sapl | 2 Fuses was
pein oan bor leit a st isbaine sad 2-00 Loup
feo" Udi dnggadatin fallnerd ty esto of the EHS
Ft wa eolfam Fyraalavite and ella ke. mel] wsyla
foreazayalkelie butyl sumer lo gure nsmsll ager the

sve nde. Phen duedacaote in berzens has alo been
te esidlzn vos lo hesooTunneaet homes he ye le
vary rannilerals wilh Le perish cae untae of the mpetcoengs
‘re beneane ing. Sith 1 and feasted ales ew ee
(array hls 982 yp donne Coatentlempenredngive ye de
Fusylag atalino Mie, (Saito, IMearapentonet the
Sernedine 211 ows peopoml goat af Tbs twetaniam. Lead
roncetace oxidation gave x= baazefacxm

1,3 eallaul KH eevee rigs? Cem MAH US