Supplements to the 2nd Edition (Editor S. Coffey) of

RODD'S CHEMISTRY O F

CARBON COMPOUND S

A modern comprehensive treatis e

Edited by

MARTIN F . ANSELLPh .D., D .Sc . (London) F .R .S .C . C . Chem .

Reader Emeritus, Department of Chemistry ,Queen Mary College, University of London, Great Britain

Supplement to

VOLUME IV HETEROCYCLIC COMPOUNDS

Part G :

Six-Membered Heterocyclic Compounds with a Single Nitrogen Ato min the Ring to which are Fused Two or More Carbocyclic Ring Systems ,and Six-Membered Ring Compounds where the Hetero-Atom i sPhosphorus, Arsenic, Antimony or Bismuth. Alkaloids Containing a

Six-Membered Heterocyclic Ring System

Heterocyclic Compounds : Six-Membered Heterocyclic Compounds with a Single Nitrogen Ato min the Ring to which are Fused Two or More Carbocyclic Ring Systems, and Six-Membere dRing Compounds where the Hetero-Atom is Phosphorus, Arsenic, Antimony or Bismuth .Alkaloids Containing a Six-Membered Heterocyclic Ring System

Preface VIfOfficial publications ; Scientific journals and periodicals XII IList of common abbreviations and symbols used XI V

Chapter 28. Polycyclic Compounds Comprising a Pyridine and Two or MoreCarbocyclic Rings

by J .D . HEPWORT H

1 .

Acridine and its derivatives(i) Acridines, 1 - (ii) 9,9'-Biacridines, 12 - (iii) Reduced acridines ,14 - (iv) Acridones, 20 -

2 .

Phenanthridine and its derivatives 3 0(i) Phenanthridines, 31 - (ii) Phenanthridinium salts, 35 - (iii )Reduced phenanthridines, 38 - (iv) Phenanthridones, 40 -

3. Benzoquinolines

4 8(i) Benzo[J]quinolines, 48- (ii) Benzo[g]quinolines, 53 - (iii )Benzo[h]quinolines, 58 - (iv) Benzo[d,e]quinolines, 65 -

4. Benzoisoquinolines

7 0(i) Benzo[f]isoquinolines, 70 - (ii) Benzo[g]isoquinolines, 74 - (iii)Benzo[h]isoquinolines, 76 - (iv) Benzo[d,e]isoquinolines, 78 -

5 .

Benzacridines 8 0(i) Benz[a]acridines, 81 - (ii) Benz[b]acridines, 83 - (iii)Benz[b]acridines, 85 - (iv) Dibenzo[a,c]acridines, 90 - (v)Dibenzo[a,j]acridines and dibenzo[a,i]acridines, 90 - (vi )Dibenzo[c h]acridines, 91 -

6 . Benzophenanthridines

9 3(i) Benzo[c]phenanthridines, 94 - (ii) Benzo[a]phenanthridines an dbenzo[b]phenanthridines, 99- (iii) Benzo[i]phenanthridines, 100 -(iv) Benzo[k]phenanthridines, 101 -

7 .

Naphthoquinolines and naphthoisoquinolines 102(i) Naphtho[2,3-g]quinolines, 103 - (ii) Naphtho[2,1-j]quinolines, 10 3- (iii) Naphtho[l,2-h]quinolines, 106 - (iv) Naphtho[2,1 f] -isoquinoline, 106- (v) Naphtho[l,2-h]isoquinolines, 108 - (vi )Naphtho[2,3-h ]isoquinolines, 108 - (vii) Naphtho[1,8--fg]quinolines ,109 -

Chapter 29. Six-Membered Heterocycles Containing Phosphorus, Arsenic ,Antimony, and Bismuth as a Single Heteroato m

by R . LIVINGSTON E

Introduction 11 11 . Phosphorus compounds 11 1

(a) Phosphorinane ( ph osphacyclohexane, hexahydrophosphabenzene) andits derivatives 1 1 1(i) Phosphorinanes, 111 - (ii) Phosphorinanones, 116 - (iii )Phosphorinanols, 119-

(b) Dihydro- and tetrahydro-phosphorins 12 0(c) Phosphorins, phosphabenzene, phosphinine 12 2(d) Phosphinolines and dibenzophosphorins

13 5(i) Phosphinolines, phosphanaphthalenes, benzophosphorins, 135 - (ii )Dibenzo[b,e]phosphorins (9-phosphaanthracenes), 141 - (iii) Dibenzo -[b,d]phosphorins

(9-phosphaphenanthrene),

144

-

(iv)Phosphaphenalene derivatives, 145 -

2 . Arsenic compounds 14 6(a) Arsabenzene (arsenin) and its derivatives

14 6(i) Arsabenzenes, 146 - (ii) Derivatives of arsabenzene possessing afunctional group, 150 -

(b) Arsanaphthalenes (benzoarsenins) 15 6(c) Dibenzoarsenins 15 7

(i)

Dibenzo[be]arsenins

(arsaanthracenes),

157

-

(ii )Dibenzo[bd]arsenin, 160-

(d) Miscellaneous heterocycles containing an arsabenzene ring 16 13 . Antimony compounds 16 2

(a) Mononuclear compounds 16 2(b) Fused ring compounds 16 4

4 . Bismuth compounds 16 6

Chapter 30. Pyridine and Piperidine Alkaloidsby M . SAINSBURY

1 . Alkaloids from the Achillea and Piper genera 16 92 . Miscellaneous N-acylpiperidine alkaloids 17 33 . Sedum alkaloids 17 44 . The alkaloids of Prosopis and Cassia species 17 95 . Alkaloids of tobacco 18 36 . Alkaloids from papaya 18 57 . Nuphar alkaloids 18 78 . Miscellaneous piperidines and pyridines from plant sources 18 99 . Fungal metabolites 19 7

10 . Piperidine and pyridine bases from insects 19 9(a) Ant venoms 19 9(b) Bases from bugs and beetles 20 2

11 . The pumilotoxins 20 312 . Pyridines from marine organisms 207

Chapter 31 . The Quinoline Alkaloidsby M . SAINSBUR Y

1 . Known quinolines from micro-organisms and higher plants 20 92 .

New alkaloids 21 7(a) Simple quinolines and 4-quinolinones 21 7(b) 2-Quinolinones 22 2(c) New furoquinoline and dihydrofuroquinoline alkaloids 23 5

3.

Non-rutaceous miscellaneous alkaloids 24 3

Chapter 32 . The Acridine Alkaloidsby M . SAINSBUR Y

I . New alkaloids 24 72. Acronycine dimers and trimers 25 7

Chapter 33 . The Isoquinoline Alkaloidsby K .W . BENTLEY

1. Simple isoquinolines, dihydro- and tetrahydroisoquinolines 25 92. Benzylisoquinolines 26 53. Bisbenzylisoquinolines 27 14. Cularines 28 05. Aporphines 28 36. Pavines and isopavines 29 57. Benzopyrrocolines 29 78. Berberines and tetrahydroberberines 29 89. Azaberberines 30 6

10. Secoberberines 30 71 I . Protopines 31 112. Phthalideisoquinolines 31 313. Spirobenzylisoquinolines 31 814. Indanobenzazepines 32 115. Rhoeadines 32 616. Other modified berberines 32 817. Benzophenanthridines 33 218. Ipecacuanha alkaloids 34 019. Phenylethylisoquinolines 34 420. Colchicine and its analogues 34 5

Chapter 34. Diterpenoid AlkaloidsbyA.R . PINDE R

Introduction 34 9I . X-ray diffraction analysis 35 02. Mass spectrometry 35 33. Nmr spectroscopy 35 6

(a) Proton magnetic resonance spectroscopy 35 6(b) Carbon-13 magnetic resonance spectroscopy 357

Chapter 35 . Steroidal Alkaloidsby A .R. PINDER

Introduction 39 31 . Apocynaceae alkaloids 39 4

(a) 3-Aminosteroids 39 4(b) 20-Aminosteroids 39 5

(c) 3,20-Diaminosteroids 39 6

(d) 3-Aminoconanines (conessanes) 39 7

(e) Miscellaneous alkaloids 39 9

2 . Salamandra alkaloids 39 93. Buxus alkaloids 40 24 . Pachysandra alkaloids 40 55 . Solanum alkaloids 406

(a) Spirosolane alkaloids 406

(b) Alkaloids related to 20-piperidyl-5a-pregnane 408

(c) Alkaloids related to 22-pyrrolidyl-5a-pregnane 409

(d) Alkaloids containing an indolizidine unit 41 1(e) Miscellaneous alkaloids 41 2

6 .

Veratrum and Fritillaria alkaloids 41 3(a) Piperidylpregnane and indolizidine alkaloids 41 3(b) C-Nor-D-homosteroidal alkaloids

41 5

(i) Alkamines, 415 - (ii) Ester-alkaloids, 419 -7 . Asclepiadaceae alkaloids 420

8 . Miscellaneous steroidal alkaloids 42 1

9 .

Biosynthesis of steroidal alkaloids 42 3

Index 429